As a common heterocyclic compound, it belong iron-catalyst compound,1,1′-Dibromoferrocene,1293-65-8,Molecular formula: C10Br2Fe,mainly used in chemical industry, its synthesis route is as follows.,1293-65-8
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
With the synthetic route has been constantly updated, we look forward to future research findings about 1,1′-Dibromoferrocene,belong iron-catalyst compound
Reference£º
Article; Schreiner, Claus; Jeschke, Janine; Milde, Bianca; Schaarschmidt, Dieter; Lang, Heinrich; Journal of Organometallic Chemistry; vol. 785; (2015); p. 32 – 43;,
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