Dimethylformamide → Methyl 2-fluoro-4-phenylbenzoate

Participants

Reaction Conditions

Reaction Steps

Combine methyl 4-bromo-2-fluorobenzoate (9.3 g, 40.0 mmol), phenylboronic acid (9.75 g, 80.0 mmol), and cesium fluoride (32.6 g, 100.1 mmol), DMF (190 mL) and deionized water (50 mL). Heat to 80° C. and add Pd(OAc)2 (303 g, 4.0 mmol). After 20 min, cool to room temperature, filter through HyFlo with the aid of 100 mL ethyl acetate, extract the filtrate with 2×100 mL 5% aqueous lithium chloride, 2×50 mL 1.0 M aqueous sodium hydroxide, and 2×100 mL brine. Separate the organic phase, dry over MgSO4, filter, and evaporate in vacuo to yield 8.85 g (96%) of methyl 3-fluorobiphenyl-4-carboxylate as a white solid. 1H NMR (CDCl3, 300 MHz) 8.01 (t, J=7.8 Hz, 1H), 7.58-7.62 (m, 2H), 7.41-7.51 (m, 4H), 7.37 (m, 1H), 3.96 (s, 3H); IR (cm−1, KBr): 3033, 2954, 1721, 1622, 1437, 1409, 1298, 1289, 1266, 1097; Anal calc'd for C14H11FO2: C 73.03, H 4.82; Found: C 73.06, H 4.86.

Provenance & Evidence