Methyl 4-bromo-3-fluorobenzoate → Methyl 3-fluoro-4-isobutylbenzoate

Participants

Reaction Steps

To a solution of methyl 4-bromo-3-fluorobenzoate (322 mg, 1.38 mmol) and isobutylzinc bromide (4.1 mL, 0.5 M in THF) in 10 mL of THF was added bis(tri-tert-butylphosphine)palladium(0) (14 mg, 0.03 mmol). The mixture was flushed with nitrogen three times and then stirred at rt overnight. The reaction was quenched by adding 5.0 mL of 1.0 N HCl solution and extracted with Et2O (3×20 mL). Organic layers were combined, washed with brine, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+S cartridge using 1:99 v/v EtOAc/hexanes as the eluant afforded 243 mg (84%) of the title compound: 1H NMR δ 0.92 (d, J=6.6, 6H), 1.93 (m, 1H), 2.56 (d, J=6.1, 2H), 3.91 (s, 31H), 7.21 (t, J=7.6, 11H), 7.67 (dd, J=1.5, 10.2, 11H), 7.74 (dd, J=1.6, 7.8, 11H).

Provenance & Evidence