2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3,4-Difluoro-2-hydroxybenzaldehyde

Participants

Reaction Steps

To a stirred solution of 2,3-difluoro-6-(hydroxylmethyl)phenol (2.5 g, 15.62 mmol) in dichloromethane (20 mL) was added a suspension of DDQ (5.32 g, 23.43 mmol) in dichloromethane (10 mL) at −5-0° C. The reaction mixture was stirred at room temperature overnight. TLC indicated absence of starting material. Reaction mixture was filtered through a bed of celite and the filtrate was concentrated in vacuum. The crude compound was purified by column chromatography over silica gel using dichloromethane (100%) as eluent to give the aldehyde derivative (2 g, 83% yield) MS: m/z 157 (M+1).

Provenance & Evidence