Hydrochloric Acid → 2-Fluoro-4-phenylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

Combine methyl 3-fluorobiphenyl-4-carboxylate (8.18 g, 35.5 mmol), THF (225 mL), and 1.0 M aqueous sodium hydroxide (225 mL). Heat at 50° C. for 8 h. Cool to room temperature, add 1.0 M aqueous hydrochloric acid (300 mL), and extract with 2×200 mL ethyl acetate. Separate the organic phase, dry over MgSO4, filter, and evaporate in vacuo to afford 7.12 g (93%) of 3-fluorobiphenyl-4-carboxylic acid as a white solid. 1H NMR (d6-DMSO, 300 MHz) 13.22 (br s, 1H), 7.93 (t, J=8.1 Hz, 1H), 7.74-7.78 (m, 2H), 7.60-7.66 (m, 2H), 7.40-7.52 (m, 3H); IR (cm−1, KBr): 3035, 2666, 2575, 1699, 1621, 1563, 1408, 1298, 1265, 1193, 904; Anal calc'd for C13H9FO2: C 72.22, H 4.20; Found: C 72.18, H 4.35.

Provenance & Evidence