A common heterocyclic compound, the iron-catalyst compound, name is 1,1′-Dibromoferrocene,cas is 1293-65-8, mainly used in chemical industry, its synthesis route is as follows.
1,10-Dibromoferrocene [23] (300 mg, 0.87 mmol) was dried for3hat 2*102 mbar in a Schlenk flask. Afterwards, itwas dissolved indry diethylether (2 ml) forming a clear yellow solution. In a separateSchlenk flask diethylether (4 ml) was cooled to 78 C and tertbutyllithiumin n-hexane (2.3 ml, 3.66 mmol,1.6M) was added. Thedissolved 1,10dibromoferrocene was added dropwise to the tertbutyllithiumsolution over a period of 5 min. The resulting mixturewas stirred at 78 C for 1 h. In an additional Schlenk flask NFSI(1.15 g, 3.66 mmol), which had been dried for 3 h in vacuo, wasdissolved in tetrahydrofurane (6 ml). The NFSI solutionwas added tothe reaction mixture within 2 min. Directly after the addition thesolution was quenched with NaBH4 and 20 ml 0.1 M Ca(OH)2.Pentane (50 ml)was added and the two-phase systemwas stirred for1 h. The organic phase was separated and washed 3 times withwater. All solvents were carefully removed in vacuo. The crudeproduct was filtered through alumina (Activity III, diameter 2 cm,length 25 cm) with pentane as mobile phase. After evaporation ofthe solvent, the crude product was purified by HPLC (CH3CN/H2O(70:30); isocratic). The HPLC fractions were extracted with pentane(4 20 ml). The organic phase was dried with MgSO4 and carefullyevaporated in vacuo (the product is volatile). The product was obtainedas a yellow solid.HPLC: CH3CN/H2O (70:30; isocratic). Yellow solid (20 mg,0.09 mmol, 10%);1H NMR (CDCl3): delta 4.39 (app. q, JHH, HF 2.2 Hz, 4H, CpH),3.91e3.89 (app. m, 4H, CpH). 13C NMR (CDCl3): delta 135.9 (d,1JCF 269 Hz, C1,10), 62.5 (d, 3JCF 3.8 Hz, C3,30,4,40), 57.5 (d,2JCF 15.1 Hz, C2,20,5,50). 19F{1H} NMR (CDCl3): delta 189 (s). IR (solid): cm1 3108 (w), 1463 n(C-Caromatic, vs); 1242 n(CeF, m), 1020 (m),803 (vs), 634 (m). MS (EI): m/z 222 [M], 139 [M CpF], 128[Cp2]; calcd for C10H8F2Fe 222.Anal. Calcd for C10H8F2Fe: C, 54.10;H, 3.63. Found: C, 53.33; H, 3.70., 1293-65-8
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Reference£º
Article; Bulfield, David; Maschke, Marcus; Lieb, Max; Metzler-Nolte, Nils; Journal of Organometallic Chemistry; vol. 797; (2015); p. 125 – 130;,
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