Dichloromethane → HCID 69991466, compound

Participants

Reaction Steps

[9-Borabicyclo[3.3.1]nonane dimer] (13.4 mL, 6.68 mmol) (9-BBN dimer) was added to a solution of methyl-3-butenoate (0.71 mL, 6.68 mmol) in tetrahydrofuran (2.7 mL) at 0-5° C. under an argon atmosphere, and the mixture was stirred for 4 hours. N,N-Dimethylformamide (27 mL), palladium(II) chloride, dichloromethane (130 g, 0.16 mmol), 1,3-dibromobenzene (0.77 mL, 61.37 mmol) and potassium phosphate (powdered, 1.5 g, 6.94 mmol) were added. The mixture was treated at 50° C. overnight. Water was added and the mixture extracted with diethyl ether. The extract was washed with water, brine, and dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate) gave 4-(3-bromophenyl)butyric acid methyl ester as a clear oil (0.26 mg, 16%).

Provenance & Evidence