Allyltributylstannane → HCID 57443291, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-methyl-benzoic acid methyl ester (1.330 g, 5.81 mmol) in 5 mL DMF and 50 mL acetonitrile are added allyl tri-n-butyl tin (2.12 g, 6.39 mmol), PdCl2(PPh3)2 (0.203 g, 0.29 mmol), and lithium chloride (0.493 g, 11.6 mmol). The resulting mixture is heated to 120° C. for 8 hours. The reaction is cooled to room temperature and concentrated under reduced pressure. The residue is dissolved in dichloromethane and purified via chromatography eluting with 10% ethyl acetate in hexanes to give 0.980 g (89%) of the desired product. 1H NMR (400 MHz, CDCl3) δ 7.79-7.76 (d, 1H), 7.05 (s, 1H), 7.05-7.03 (d, 1H), 6.03-5.92 (m, 1H), 5.01 (dd, 1H), 4.99-4.98 (dd, 1H), 3.84 (s, 3H), 3.72 (dd, 1H), 3.70 (dd, 1H), 2.33 (s, 3H).

Provenance & Evidence