Category: 1293-65-8

1293-65-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,1′-Dibromoferrocene, cas is 1293-65-8,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.

Part ( I)Preparation of 1-bromo-l’ -trimethylsilyl ferroceneTo 1, 1 ‘-dibromoferrocene (1Og, 29.08mmol) in dry THF (200ml) cooled to -780C (dry ice/acetone bath) was added n-butyllithium (11.05ml, 27.63mmol, 0.95eq) and the reaction was stirred under N2 for 30 min. Chlorotrimethylsilane (3.7ml, 29.08mmol, leq) was then added dropwise and the solution was then allowed to warm up to room temperature and further stirred for twelve hours resulting in a red solution.The reaction was then quenched with water, and stirred for a further fifteen minutes. The ethereal layer, containing product was separated and the aqueous layer was further extracted several times with diethyl ether. The combined ether fractions were dried over magnesium sulphate and filtered through celite. The ether solvent was removed by rotary evaporator (resulting in red oil) . The product was purified as the initial red band (petrol) by column chromatography. The resulting red oil was finally dried under vacuum: (7.11g, 73 % yield) .

The chemical industry reduces the impact on the environment during synthesis,1293-65-8,1,1’-Dibromoferrocene,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; LUCITE INTERNATIONAL UK LIMITED; WO2008/65448; (2008); A1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

It is a common heterocyclic compound, the iron-catalyst compound, 1,1′-Dibromoferrocene, cas is 1293-65-8 its synthesis route is as follows.

1 ,1 ‘-Dibromoferrocene (0.67 g, 1.97 mmol) in anhydrous tetrahydrofuran (THF) (30 ml) was placed in a reaction vessel and cooled to -78 0C using a dry ice and acetone mixture, n-butyl lithium (0.94 ml, 2.36 mmol) was added under inert conditions thereto and the contents of the reaction vessel kept stirred for approximately 1 hour while cold zinc chloride (2.16 ml, 2.16 mmol) was added. Tetrakis(triphenylphosphine)palladiumO (50 mg) and 4-iodophthalonitrile (0.5 g, 1.97 mmol) were then added. The contents of the reaction vessel were allowed to warm to room temperature and were kept stirred for approximately 16 hours. Thereafter, water (20 ml) was added and extracted with dichloromethane (3 x 20 ml). The combined organic layers were dried over magnesium sulfate and reduced to dryness under reduced pressure to obtain a crude product. The crude product was placed on alumina and eluted with diethyl ether ; petroleum spirit (55:45) to yield red crystals.

1293-65-8, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,1293-65-8 ,1,1′-Dibromoferrocene, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; CORUS UK LIMITED; HOLLIMAN, Peter; RUGEN-HANKEY, Sarah; WO2010/136178; (2010); A1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

1293-65-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,1′-Dibromoferrocene, cas is 1293-65-8,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.

Under a nitrogen atmosphere,2.0370 g (5.924 mmol) of 1,1′-dibromoferrocene was dissolved in THF (50 ml)Under cooling at -78 C.,4.0 ml (6.516 mmol) of n-butyllithium (1.6 M, n-hexane solution) was added and the mixture was stirred for 20 minutes.ThenN, N-dimethylmethylene ammonium iodide2.2 g (11.848 mmol) was added, then the mixture was allowed to stand at room temperature and stirred for 16 hours.An ammonium chloride aqueous solution (100 ml) and chloroform (150 ml) were added to the reaction solution, and the mixture was separated. The aqueous phase was further extracted twice with 50 ml of chloroform.The obtained organic phase (250 ml) was washed with saturated brine,After drying over sodium sulfate, concentration under reduced pressure gave a crude product. This was purified by silica gel column chromatography to obtain 1.6692 g (5.1835 mmol, yield 87.5%) of 1-bromo-1 ‘- ((dimethylamino) methyl) ferrocene as an intermediate.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,1’-Dibromoferrocene, 1293-65-8

Reference£º
Patent; Shimane Prefecture; Kyushu Institute of Technology; KNC Laboratories Co., Ltd; Imawaka, Naoto; Matsubayashi, Kazuhiko; Oda, Yukiko; Sakamoto, Rumi; Takenaka, Shigeori; Sato, Shinobu; Tanaka, Koichi; Uno, Takuya; Nobukuni, Hirofumi; (20 pag.)JP2018/203652; (2018); A;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

1293-65-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,1′-Dibromoferrocene, cas is 1293-65-8,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.

A) Preparation of Intermediates; EXAMPLE A1; Preparation of (Rc,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1′-bromoferrocene of the formula (A1) [Ph=phenyl; Me=methyl]; a) Preparation of 1-phenylchlorophosphino-1′-bromoferrocene (X1); 14.5 ml (23.2 mmol) of n-BuLi (1.6 M in hexane) are added dropwise to a solution of 8 g (23.2 mmol) of 1,1′-dibromoferrocene in 30 ml of THF at a temperature of <-30 C. The mixture is stirred for another 30 minutes at this temperature. It is then cooled to -78 C. and 3.15 ml (23.2 mmol) of phenyldichlorophosphine are added dropwise at such a rate that the temperature does not exceed -60 C. After stirring at -78 C. for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. This gives a suspension of the monochlorophosphine X1.; b) Preparation of 1-bromo-1'-lithioferrocene X5; 4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.43 g (10 mmol) of 1,1'-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of <-30 C. The mixture is stirred at this temperature for another 1.5 hours and subsequently cooled to -78 C. This gives a suspension of 1-bromo-1'-lithioferrocene X5.; Reaction mixture b): In a second reaction flask, 4.0 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.43 g (10 mmol) of 1,1'-dibromo-ferrocene in 10 ml of THF which has cooled to -30 C. at such a rate that the temperature does not exceed -30 C. The mixture is subsequently stirred at -30 C. for a further 1.5 hours and the mixture containing the 1-bromo-1'-lithioferrocene is finally cooled to -78 C. The chemical industry reduces the impact on the environment during synthesis,1293-65-8,1,1'-Dibromoferrocene,I believe this compound will play a more active role in future production and life. Reference£º
Patent; Chen, Weiping; Spindler, Felix; Nettekoven, Ulrike; Pugin, Benoit; US2010/160660; (2010); A1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

It is a common heterocyclic compound, the iron-catalyst compound, 1,1′-Dibromoferrocene, cas is 1293-65-8 its synthesis route is as follows.

1 ,1 ‘-Dibromoferrocene (0.67 g, 1.97 mmol) in anhydrous tetrahydrofuran (THF) (30 ml) was placed in a reaction vessel and cooled to -78 0C using a dry ice and acetone mixture, n-butyl lithium (0.94 ml, 2.36 mmol) was added under inert conditions thereto and the contents of the reaction vessel kept stirred for approximately 1 hour while cold zinc chloride (2.16 ml, 2.16 mmol) was added. Tetrakis(triphenylphosphine)palladiumO (50 mg) and 4,5- dichlorophthalonitrile (0.5 g, 1.97 mmol) were then added. The contents of the reaction vessel were allowed to warm to room temperature and were kept stirred for approximately 2 hours before heating to approximately 90 0C for 12 hours. Thereafter, water (20 ml) was added and extracted with dichloromethane (3 x 20 ml). The combined organic layers were dried over magnesium sulfate and reduced to dryness under reduced pressure to obtain a crude product. The crude product was placed on alumina and eluted with diethyl ether ; petroleum spirit (55:45) to yield red crystals.

1293-65-8, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,1293-65-8 ,1,1′-Dibromoferrocene, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; CORUS UK LIMITED; HOLLIMAN, Peter; RUGEN-HANKEY, Sarah; WO2010/136178; (2010); A1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

1293-65-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,1′-Dibromoferrocene, cas is 1293-65-8,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.

1,10-Dibromoferrocene [23] (1.8 g, 5.2 mmol) was dried for 3 h at2 * 102 mbar. Subsequently it was dissolved in dry tetrahydrofuran(20 ml) and cooled to 78 C, causing a clear orange solution. Nbutyllithiumin n-hexane (3.7 ml, 5.6 mmol, 1.6 M) was addedslowly over 15 min. The resulting suspension was stirred for anadditional 30 min. In a second Schlenk flask, a suspension of NFSI(1.81 g, 5.8 mmol, dried for 3 h in vacuo) in diethylether (20 ml) wasprepared. After 30 min the reaction mixture was transferred intothe NFSI solution via cannula. Directly after the addition the solutionwasquenched with NaBH4 and 50 ml of 0.1MCa(OH)2, and theresulting slurry was diluted with hexane (100 ml). The two phasesystem was stirred for 1 h, the organic phase was separated andwashed three times with water. After evaporation of the solvent invacuo, the resulting brown oil was dissolved again in 50 ml ofhexane and the organic phasewas extracted thrice with 0.2MFeCl3solution and subsequently 3 times with water. The organic phasewas filtered through alumina (Activity III, diameter 2 cm, length25 cm) and dried with MgSO4. After the solvents were evaporatedthe crude product was purified by HPLC (isocratic CH3CN/H2O(70:30); isocratic). The HPLC fractions were extracted with hexane(4 20 ml). The organic phase was dried with MgSO4 and evaporatedin vacuo, leaving the product as a browneorange oil.HPLC: CH3CN/H2O (70:30; isocratic). Browneorange oil (674 mg,2.40 mmol, 46%);1H NMR (CDCl3): delta 4.51 (app. s, 2H, CpH, H2?,5?), 4.33 (app. s, 2H,CpH,H2,5), 4.21 (app. s, 2H, CpH,H3?,4?), 3.88 (app. s, 2H, CpH,H3,4). 13CNMR (CDCl3): delta 135.6 (d, 1JCF 270 Hz, C1), 78.1 (s, C1?), 71.6 (s, C2?,5?),68.6 (s, C3?,4?), 64.0 (d, 3JCF 3.8 Hz, C3,4), 58.7 (d, 2JCF 15.0 Hz, C2,5).19F{1H} NMR (CDCl3): delta 189 (s). IR (ATR): cm-1 3110 (w), 1471 n(CCaromatic,vs); 1242 n(CeF, m),1152 (m), 807 (vs), 657 (m).MS(EI): m/z282 [M], 128 [Cp2]; calcd for C10H8FBrFe 282. Anal. Calcd forC10H8FBrFe: C, 42.45; H, 2.85. Found: C, 42.26; H, 2.86.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,1′-Dibromoferrocene, 1293-65-8

Reference£º
Article; Bulfield, David; Maschke, Marcus; Lieb, Max; Metzler-Nolte, Nils; Journal of Organometallic Chemistry; vol. 797; (2015); p. 125 – 130;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

1293-65-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,1′-Dibromoferrocene, cas is 1293-65-8,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,1?-dibromo ferrocene (1, 2.58 g, 7.50 mmol, 1.0 equiv) dissolved in tetrahydrofuran (40 mL) a 2.5 M solution of n-butyl lithium in hexane (2.85 mL, 7.13 mmol, 0.95 equiv) was added dropwise at-70 C. After stirring the reaction solution at this temperature for 1 h, chlorodi-2-(5-methyl)furyl phosphine (2c) (1.71 g, 7.50 mmol) was added in a single portion. The reaction mixture was stirred for 1 h at ambient temperature and was then concentrated in oil pump vacuum. The resulting residue was purified by column chromatography on alumina using a mixture of hexane-diethyl ether (ratio 5:1; v/v). After drying in oil pump vacuum the title compound was obtained as a pale yellow solid. Please, note that 3c could not be completely separated from P(Fc)(2-(5-Me)C4H2O)2 formed as by-product and hence was used without additional purification in further reactions. Anal. Calcd. for C20H18BrFeO2P (457.08 g/mol): C, 52.55; H, 3.97. Found: C, 54.22*; H 3.92*. Mp.: 77 C. IR (NaCl, /cm-1): 1019 (s, C-O-C), 1410/1446/1496/1593 (w, C=C), 2920/2951 (w, C-H), 3109 (w, =C-H). 1H NMR (500.30MHz, CDCl3, delta): 2.36 (s, 6H, CH3), 3.99 (pt, 3/4JHH=1.9Hz, 2H, Hbeta/C5H4Br), 4.31 (pt, 3/4JHH=1.9Hz, 2H, Halpha/C5H4Br), 4.38 (dpt, 4JPH=0.6Hz, 3/4JHH=2.0Hz, 2H, Hbeta/C5H4P), 4.47 (dpt, 3JPH=1.8Hz, 3/4JHH=2.0Hz, 2H, Halpha/C5H4P), 5.99 (ddq, 4JPH=1.4Hz, 3JHH=3.1Hz, 4JHH=1.0Hz, 2H, H4/5-MeC4H2O), 6.59 (ddq, 3JPH=1.9Hz, 3JHH=3.1Hz, 5JHH=0.2Hz, 2H, H3/5-MeC4H2O). 13C{1H} NMR (125.81MHz, CDCl3, delta): 14.1 (s, CH3), 68.5 (s, Cbeta/C5H4Br), 71.2 (s, Calpha/C5H4Br), 74.0 (d, 3JCP=5Hz, Cbeta/C5H4P), 75.5 (d, 1JCP=3Hz, Ci/C5H4P), 75.8 (d, 2JCP=18Hz, Calpha/C5H4P), 77.9 (s, Ci/C5H4Br), 107.0 (d, 3JCP=6Hz, C4/5-MeC4H2O), 121.1 (d, 2JCP=22Hz, C3/5-MeC4H2O), 150.2 (d, 1JCP=4Hz, C2/5-MeC4H2O), 156.7 (d, 3JCP=3Hz, C5/5-MeC4H2O). 31P{1H} NMR (202.5MHz, CDCl3, delta):-66.7 (s). *) The sample included 15% 1-di(2-(5-methylfuryl)phosphanyl)ferrocene (4b) which could not be separated from the title compound

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1293-65-8, 1,1′-Dibromoferrocene

Reference£º
Article; Schreiner, Claus; Jeschke, Janine; Milde, Bianca; Schaarschmidt, Dieter; Lang, Heinrich; Journal of Organometallic Chemistry; vol. 785; (2015); p. 32 – 43;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

As a common heterocyclic compound, it belongs to iron-catalyst compound, name is 1,1′-Dibromoferrocene, and cas is 1293-65-8, its synthesis route is as follows.,1293-65-8

1,10-Dibromoferrocene [23] (1.8 g, 5.2 mmol) was dried for 3 h at2 * 102 mbar. Subsequently it was dissolved in dry tetrahydrofuran(20 ml) and cooled to 78 C, causing a clear orange solution. Nbutyllithiumin n-hexane (3.7 ml, 5.6 mmol, 1.6 M) was addedslowly over 15 min. The resulting suspension was stirred for anadditional 30 min. In a second Schlenk flask, a suspension of NFSI(1.81 g, 5.8 mmol, dried for 3 h in vacuo) in diethylether (20 ml) wasprepared. After 30 min the reaction mixture was transferred intothe NFSI solution via cannula. Directly after the addition the solutionwasquenched with NaBH4 and 50 ml of 0.1MCa(OH)2, and theresulting slurry was diluted with hexane (100 ml). The two phasesystem was stirred for 1 h, the organic phase was separated andwashed three times with water. After evaporation of the solvent invacuo, the resulting brown oil was dissolved again in 50 ml ofhexane and the organic phasewas extracted thrice with 0.2MFeCl3solution and subsequently 3 times with water. The organic phasewas filtered through alumina (Activity III, diameter 2 cm, length25 cm) and dried with MgSO4. After the solvents were evaporatedthe crude product was purified by HPLC (isocratic CH3CN/H2O(70:30); isocratic). The HPLC fractions were extracted with hexane(4 20 ml). The organic phase was dried with MgSO4 and evaporatedin vacuo, leaving the product as a browneorange oil.HPLC: CH3CN/H2O (70:30; isocratic). Browneorange oil (674 mg,2.40 mmol, 46%);1H NMR (CDCl3): delta 4.51 (app. s, 2H, CpH, H2?,5?), 4.33 (app. s, 2H,CpH,H2,5), 4.21 (app. s, 2H, CpH,H3?,4?), 3.88 (app. s, 2H, CpH,H3,4). 13CNMR (CDCl3): delta 135.6 (d, 1JCF 270 Hz, C1), 78.1 (s, C1?), 71.6 (s, C2?,5?),68.6 (s, C3?,4?), 64.0 (d, 3JCF 3.8 Hz, C3,4), 58.7 (d, 2JCF 15.0 Hz, C2,5).19F{1H} NMR (CDCl3): delta 189 (s). IR (ATR): cm-1 3110 (w), 1471 n(CCaromatic,vs); 1242 n(CeF, m),1152 (m), 807 (vs), 657 (m).MS(EI): m/z282 [M], 128 [Cp2]; calcd for C10H8FBrFe 282. Anal. Calcd forC10H8FBrFe: C, 42.45; H, 2.85. Found: C, 42.26; H, 2.86.

1293-65-8 is used more and more widely, we look forward to future research findings about 1,1′-Dibromoferrocene

Reference£º
Article; Bulfield, David; Maschke, Marcus; Lieb, Max; Metzler-Nolte, Nils; Journal of Organometallic Chemistry; vol. 797; (2015); p. 125 – 130;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

Name is 1,1′-Dibromoferrocene, as a common heterocyclic compound, it belongs to iron-catalyst compound, and cas is 1293-65-8, its synthesis route is as follows.,1293-65-8

In a Schlenk tube CuI (100 mg, 0.53 mmol), PPh3 (1.60 mmol),1,1?-dibromoferrocene (1.8 g, 5.2 mmol), 4-t-butylphenol(1.02 g, 1.3 eq.), and Cs2CO3 (1.86 g, 1.1 eq.) were dissolved in toluene (35 mL), and the reaction mixture was stirred at 110 C for 26 h. After evaporation of the volatiles, the crude product was purified by silica column chromatography (cyclohexane-ethyl acetate). Of a light-yellow fraction, the solvent was removed, which resulted in 930 mg (43 %) of a yellow-brownish solid. – Rf = 0.65 [cyclohexane-ethylacetate (20:1)]. – 1H NMR (CDCl3): delta = 1.22 (s, 9 H; CH3), 3.95 (t, J = 1.9 Hz, 4 H, Cp), 4.21 (t, J = 1.9 Hz, 4 H, Cp), 6.87 (d,J = 8.6 Hz, 2 H, phenyl H2, H6), 7.19 ppm (d, J = 8.6 Hz, 2 H,phenyl H3, H5). – 13C NMR (75 MHz, CDCl3): delta = 31.7 (CH3), 34.4 (CCH3), 60.8 (C5H4), 64.2 (C5H4), 68.2, 68.8, 77.6, 117.0,123.2, 126.2, 145.4, 156.4 ppm.

With the complex challenges of chemical substances, we look forward to future research findings about 1,1′-Dibromoferrocene

Reference£º
Article; Frey, Guido D.; Hoffmann, Stephan D.; Zeitschrift fur Naturforschung – Section B Journal of Chemical Sciences; vol. 70; 1; (2015); p. 65 – 70;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

Name is 1,1′-Dibromoferrocene, as a common heterocyclic compound, it belongs to iron-catalyst compound, and cas is 1293-65-8, its synthesis route is as follows.,1293-65-8

1 ,1 ‘-Dibromoferrocene (0.67 g, 1.97 mmol) in anhydrous tetrahydrofuran (THF) (30 ml) was placed in a reaction vessel and cooled to -78 0C using a dry ice and acetone mixture, n-butyl lithium (0.94 ml, 2.36 mmol) was added under inert conditions thereto and the contents of the reaction vessel kept stirred for approximately 1 hour while cold zinc chloride (2.16 ml, 2.16 mmol) was added. Tetrakis(triphenylphosphine)palladiumO (50 mg) and 4,5- dichlorophthalonitrile (0.5 g, 1.97 mmol) were then added. The contents of the reaction vessel were allowed to warm to room temperature and were kept stirred for approximately 2 hours before heating to approximately 90 0C for 12 hours. Thereafter, water (20 ml) was added and extracted with dichloromethane (3 x 20 ml). The combined organic layers were dried over magnesium sulfate and reduced to dryness under reduced pressure to obtain a crude product. The crude product was placed on alumina and eluted with diethyl ether ; petroleum spirit (55:45) to yield red crystals.

With the complex challenges of chemical substances, we look forward to future research findings about 1,1’-Dibromoferrocene

Reference£º
Patent; CORUS UK LIMITED; HOLLIMAN, Peter; RUGEN-HANKEY, Sarah; WO2010/136178; (2010); A1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion