Allyltributylstannane → HCID 57443291, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-bromo-4-methylbenzoate (500 mg, 2.183 mmol), allyltributylstannane (0.744 mL, 2.401 mmol), lithium chloride (185 mg, 4.37 mmol) in DMF (1 mL), acetonitrile (10 mL) was added bis(triphenylphosphine)palladium(ii) dichloride (77 mg, 0.109 mmol). It was then degassed for 2 min, then filled with N2. After heating at 90° C. for 16 h, it was quenched with NH4Cl, extracted with EtOAc. The organic layer was washed with KF solution, dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate methyl 2-allyl-4-methylbenzoate (330 mg, 1.735 mmol, 79% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.95-7.77 (m, 1H), 7.21-6.99 (m, 2H), 6.19-5.85 (m, 1H), 5.22-4.91 (m, 2H), 3.89 (s, 3H), 3.76 (d, J=6.6 Hz, 2H), 2.39 (s, 3H).

Provenance & Evidence