Sodium Bicarbonate → 1-(2,6-Difluoro-4-iodophenyl)ethan-1-one

Participants

Reaction Steps

To a solution of 1-(2,6-difluoro-4-iodo-phenyl)-ethanol (561 mg, 1.98 mmol) in methylene chloride (25 mL) cooled in an ice/water bath were added 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) (3 mg, 0.12 mmol), sodium hydrogen carbonate (75 mg, 0.89 mmol) and tetrabutylammonium bromide (19 mg, 0.06 mmol). To this resulting mixture was added a 5% aqueous sodium hypochlorite solution in a dropwise manner until TLC indicated the reaction to be complete. The reaction mixture was diluted with methylene chloride (50 mL) and brine (100 mL) and the organic layer separated. The organic layer was dried over sodium sulfate, filtered through a pad of silica gel and concentrated in vacuo to give 1-(2,6-difluoro-4-iodo-phenyl)-ethanone (526 mg, 94%). HR-MS: calcd for C29H25F2IN4O4 [M+H+] 659.0962. Found 659.0962.

Provenance & Evidence