Oxygen → 4-Fluoro-2-(hydroxymethyl)phenol

Participants

Reaction Conditions

Reaction Steps

27.1 g (159.28 mmol) of methyl 5-fluoro-2-hydroxybenzoate are introduced into 500 ml of dry THF with exclusion of oxygen and cooled to 0° C. Subsequently, while cooling, 238 ml (238 mmol) of a 1 M solution of lithium aluminium hydride in THF are slowly added dropwise, and the mixture is stirred at 0° C. for 1 hour and then at RT overnight. After reaction is complete, saturated ammonium chloride solution is added to the mixture, and it is taken up in dichloromethane. The organic phase is separated off and dried over sodium sulphate. After filtration, the solvent is removed in vacuo. The crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1). 18.0 g (126.6 mmol, 79% of theory) of a colourless solid are isolated.

Provenance & Evidence