(2,4-difluoro-5-methylphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4-difluoro-5-methyl-benzoic acid methyl ester from Step A (1.0 g, 5.37 mmol) in tetrahydrofuran (10 mL), cooled to −78° C. using a dry ice/acetone bath, was added lithium aluminum hydride, 1.0M in tetrahydrofuran (10 mL, 10 mmol), in a dropwise manner. The solution was stirred for two hours. The reaction was quenched by dropwise addition of ice-cold saturated sodium bicarbonate solution, allowed to warm to room temperature and was extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a colorless liquid (1.0 g, quantitative yield). The reaction was quenched by dropwise addition of ice-cold saturated sodium bicarbonate solution was extracted with ethyl acetate The organic layer was washed with water and brine dried over magnesium sulfate The slurry was filtered concentrated