Dimethylformamide → HCID 19086784, compound

Participants

Reaction Steps

1.068 g (6.2 mmole) of 2-chloro-4'-fluoroacetophenone were dissolved in 20 ml of diethyl ether, and the ethereal solution was stirred under a stream of nitrogen, whilst 7.5 ml of an ethereal solution containing 7.4 mmole of trimethylsilylmethylmagnesium chloride was added dropwise at such a rate that the temperature of the reaction mixture did not exceed -10° C. to -5° C. The reaction mixture was then stirred for a further 15 minutes whilst being kept within this temperature range. At the end of this time, 3.5 ml of dimethylformamide were added dropwise to the reaction solution at such a rate that the temperature of the reaction mixture did not exceed -10° C. to -5° C. The reaction mixture was then stirred for a further 10 minutes and, whilst it was being kept within this temperature range, 6 ml of hexane and then 6 ml of water were added. The reaction mixture was then stirred for 5 minutes, after which it was poured into 10 ml of water and extracted with 100 ml of hexane. The organic extract was washed with 50 ml of a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.39 g (yield 100%) of the title compound, as an oily substance.

Provenance & Evidence