Hydrochloric Acid → 4-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acid

Participants

Reaction Steps

To a solution of methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoate (1.80 g, 4.05 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.85 g, 20.30 mmol) in water (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. After addition of 1 N hydrochloric acid (10 mL) and ethyl acetate (150 mL), the organic phase was separated, washed with 1 N hydrochloric acid (10 mL) and brine (10 mL); dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo yielded the title compound (1.75 g, quant) as an off-white solid, which was used without further purification: MS (ES−) m/z 429.1 (M−1).

Provenance & Evidence