(Dimethyl sulfide)trihydroboron → 2,3-Difluoro-4-(2-hydroxyethyl)phenol

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Reaction Steps

A solution of borane dimethylsulfide complex (2M in THF, 14.4 mL) was added dropwise to a solution of 2-(2,3-difluoro-4-hydroxyphenyl)acetic acid (example 77, step a) (1.08 g) in tetrahydrofuran (25 mL) at 0° C. and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with methanol and when bubbling had ceased the solvent evaporated. The residue was purified by silica gel chromatography eluting with 4:1 isohexane:ethyl acetate to ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as white solid. Yield 0.95 g.

Provenance & Evidence