4-Hydroxybenzoic Acid → HCID 28604971, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxybenzoic acid (7 g, 50 mmol) and 2-fluorobenzonitrile (7.36 g, 60 mmol) in dimethylsulfoxide (40 mL) was added potassium carbonate (20 g, 150 mmol). The reaction mixture was stirred at 120° C. for 4 hours. After the reaction, the temperature was allowed to cool to room temperature, then the mixture was poured into ice water (100 mL). The mixture was neutralized to pH=3 with concentrated hydrochloric acid and then extracted with ethyl acetate (15 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give 4-(2-cyanophenoxy)benzoic acid as a white solid (5.80 g, 48.5%). LRMS (M+H)− m/z: calcd 239.06. found 239. 1H NMR (300 MHz, d6-DMSO): δ 12.94 (s, 1H), 7.99-7.91 (m, 3H), 7.71 (t, J=8.4 Hz, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.17-7.14 (m, 3H).

Provenance & Evidence