Allyltributylstannane → 2-Allyl-5-methoxy-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of 2-Bromo-5-methoxy-benzoic acid methyl ester (750 mg, 3.02 mmol) in benzene (2 mL) are added allyltri-n-butyl tin (1.16 mL, 3.73 mmol) and tetrakis(triphenylphosphine)palladium (0) (174 mg, 0.157 mmol, 5 mol %). The reaction mixture is heated in a sealed tube to 100° C. After 3 h, the reaction is concentrated under reduced pressure and the residue is chromatographed (0% to 10% EtOAc/Hex) to yield the title compound (451 mg, 73%). 1H NMR (400 MHz, CDCl3) δ 7.40 (d, 1H, J=2.6 Hz), 7.18 (d, 1H, J=8.4 Hz), 7.00 (dd, 1H, J=8.6, 2.9 Hz), 6.04-5.93 (m, 1H), 5.03-4.94 (m, 2H), 3.88 (s, 3H), 3.82 (s, 3H), 3.70-3.65 (m, 2H).

Provenance & Evidence