Sodium Carbonate → Methyl 2'-fluoro-4'-methoxy-2-methylbiphenyl-4-carboxylate

Participants

Reaction Steps

A mixture of 4-bromo-3-fluoro anisole (500 mg, 2.44 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (INTERMEDIATE 37, 875 mg, 3.17 mmol), tetrakis(triphenylphosphine) palladium (282 mg, 5% mol) and Na2CO3 (569 mg, 5.37 mmol) in 20 mL of water/EtOH/toluene (1:2:4) was heated at reflux for 4 h. TLC (CH2Cl2/hexane (1:1)) showed that the reaction was complete. The solvents were removed. Water (10 mL) was added. The organic was extracted with CH2Cl2 (3×10 mL). The combined CH2Cl2 layers were washed with brine and then dried (Na2SO4). The title compound was obtained after flash chromatography using CH2Cl2/hexanes (6:4) as the eluent. 1H NMR (500 MHz, CDCl3): δ 7.98 (s, 1H), 7.92 (dd, J=8.0, 1.5 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.16 (t, J=8.5 Hz, 1H), 6.80 (dd, J=8.5, 2.5 Hz, 1H), 6.77 (dd, J=11.5, 2.5 Hz, 1H), 3.95 (s, 3H), 3.88 (s, 3H), 2.28 (s, 3H).

Provenance & Evidence