(4-Benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester → (1-Bromo-6-fluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester

Participants

Reaction Steps

To a solution of (4-benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (400 mg, 0.992 mmol) in ethyl acetate (10 mL) was added zinc bromide (670 mg, 2.978 mmol) and 10% palladium on carbon (40 mg) under a hydrogen atmosphere (balloon). After being stirred at room temperature for 1 hour, the resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC (gradient elution with 50-80% 0.1% trifluoroacetic acid in water in acetonitrile, 8 minutes) to afford (1-bromo-6-fluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester (200 mg, 64.4%) as a white solid.

Provenance & Evidence