Diethyl Ether → HCID 67970696, compound

Participants

Reaction Steps

Purge a mixture of 3-bromo-4-(difluoromethyl)benzonitrile (8.87 g, 38.2 mmol, 1.0 equiv), triethylamine (16.0 mL, 114.7 mmol, 3.0 equiv), methanol (70 mL), and DMF (120 mL) with nitrogen, then treat the mixture with palladium(II) acetate (867 mg, 3.82 mmol, 0.1 equiv) and 1,3-bis(diphenylphosphino)propane (1.61 g, 3.82 mmol, 0.1 equiv). Stir the mixture under 138 kPaG of carbon monoxide at room temperature for two days and then 80° C. for one day. Cool the mixture to room temperature and dilute with Et2O (300 mL). Wash the mixture with water and saturated aqueous NaCl, and separate the organic layer. Dry the organic layer over sodium sulfate, filter, and concentrate under reduced pressure. Subject the resulting crude material to chromatography on silica gel eluting with a 10-15% THF/hexanes gradient to give the title compound (6.19 g, 77%). GC/MS (m/z) 211 (M).

Provenance & Evidence