3-Fluoro-4-hydroxybenzeneacetic acid → Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

Participants

Reaction Steps

To a solution of (3-fluoro-4-hydroxy-phenyl)-acetic acid (20 g, 117.5 mmol) in MeOH (150 mL), was H2SO4 (3 drops) added. The reaction mixture was heated to reflux and maintained for 2 hours. The reaction was cooled to room temperature and 5 g of NaHCO3 was added portionwise. The reaction was concentrated under vacuum and dissolved in ether (200 mL). The ether layer was washed with sat. NaHCO3. The ether layer was dried over MgSO4, and concentrated under vacuum to afford the desired compound (19.9 g, 92%) as an oil. The crude compound was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.92 (s, 1H), 7.01-7.20 (m, 2H), 3.62 (s, 2H), 3.61 (s, 3H). LCMS 185.1 [MH+].

Provenance & Evidence