Dichloromethane → HCID 59570036, compound

Participants

Reaction Steps

A stirred solution of dimethyl 5-bromoisophthalate (273 mg, 1.0 mmol), potassium vinyltrifluoroborate (134 mg, 1.0 mmol) PdCl2(dppf).CH2Cl2 (16.3 mg, 0.02 mmol) and Et3N (0.42 mL, 3.0 mmol) in i-PrOH (6 mL) and H2O (3 mL) was heated to reflux for 3 h. The solution was cooled to room temperature and diluted with EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (8% EtOAc in hexanes) to provide dimethyl 5-vinylisophthalate (153.6 mg, 70%).

Provenance & Evidence