Methyl 4'-bromo[1,1'-biphenyl]-4-carboxylate

619-44-3

5467-74-3

89901-03-1

Methyl 4-iodobenzoate (9.38 g, 35.8 mmol) and 4-bromophenylboronic acid (7.18 g, 35.8 mmol) were added to Pd(PPh3)4 (2.07 g, 1.79 mmol) in a solvent mixture of toluene (180 mL) and ethanol (100 mL) to form a clarified solution. To this solution was added 4.0 M aqueous sodium carbonate (30 mL). The reaction mixture was refluxed at 80°C for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed sequentially with water (2 x 300 mL), saturated aqueous NaHCO3 (2 x 300 mL) and saturated aqueous NaCl, and then dried over MgSO4. After concentrating the organic phase, the residue was purified by column chromatography (eluent: 7% ethyl acetate-heptane) to afford the white solid product methyl 4'-bromo[1,1'-biphenyl]-4-carboxylate (7.8 g, 78% yield).1H NMR (CDCl3) δ: 8.10 (d, 2H, J = 9.0 Hz), 7.62 (d, 2H, J = 9.0 Hz), 7.59 (d, 2H, J = 9.0 Hz), 7.59 (d, 2H, J = 9.0 Hz), 7.59 (d, 2H, J = 9.0 Hz) 7.59 (d, 2H, J = 9.3 Hz), 7.48 (d, 2H, J = 9.3 Hz), 3.95 (s, 3H).