Allyltributylstannane → 3-Allyl-4-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled into a solution of methyl 3-bromo-4-methylbenzoate (11.45 g, 50 mmol), allyltributyl-stannane (16.72 g, 50.5 mmol) and lithium chloride (5.30 g, 125 mmol) in DMF (100 mL) with magnetic stirring for 20 minutes. Dichlorobis(triphenyl-phosphine)palladium (0.81 g, 1.16 mmol) was then added and mixture heated at 95° C. for 1.5 hours. After cooling to room temperature, the mixture was partitioned between ether-hexanes (1:1 V/V) and water. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Isco RediSep 330 g silica gel, 5% then 35% dichloromethane in hexanes) to give 3-allyl-4-methyl-benzoic acid methyl ester (9.68 g, 100%) as a colorless oil.

Provenance & Evidence