Ammonium Chloride → 1-(4-Bromo-2-methylphenyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-N-methoxy-2,N-dimethyl-benzamide (886 mg, 3.43 mmol) in anhydrous tetrahydrofuran (20 mL) at −60° C. under an atmosphere of nitrogen was added 3.0 M methylmagnesium chloride in tetrahydrofuran (1.26 mL, 3.78 mmol) via syringe. The reaction was stirred for 20 minutes at −60° C., then at room temperature for 30 minutes. Saturated aqueous ammonium chloride solution was added, the mixture was poured into a separatory funnel and extracted with diethyl ether (3×50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(4-bromo-2-methyl-phenyl)-ethanone (700 mg, 96%). HR-MS: calcd for C30H29BrN4O4 [M+H+] 589.1445. Found 589.1445.

Provenance & Evidence