2-Fluoro-5-hydroxybenzaldehyde → 4-Fluoro-3-(hydroxymethyl)phenol

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Reaction Steps

to a stirred solution of 2-fluoro-5-hydroxybenzaldehyde (4.1 g) in methanol (50 mL) at 0° C. was added portionwise sodium borohydride (0.55 g). The mixture was warmed to room temperature, stirred for 1 hour then partitioned between water (200 mL) and ethyl acetate (2×200 mL). The combined organics were washed (brine), dried (magnesium sulfate) and concentrated to give 2-fluoro-5-hydroxybenzyl alcohol as a yellow oil which crystallised on standing overnight (4.1 g, 95% yield):

Provenance & Evidence