Sodium Carbonate → HCID 67146652, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.96 g, 2.8 mmol), bis(pinacolato)diboron (0.77 g, 3.0 mmol) and potassium acetate (0.81 g, 8.3 mmol) were dissolved in N,N-dimethylformamide (30 mL) and, after argon substitution, 1,1′-bis(diphenyphosphino)ferrocenedichloropalladium (II) (0.067 g, 0.083 mmol) was added. The reaction mixture was heated overnight under an argon atmosphere at 80° C. The reaction mixture was cooled, and 3-bromothiophene (0.43 g, 2.6 mmol), 1,1′-bis(diphenyphosphino)ferrocenedichloropalladium (II) (0.067 g, 0.083 mmol) and 2N aqueous sodium carbonate solution (6.9 mL, 14 mmol) were added to the reaction mixture. The reaction mixture was heated overnight under an argon atmosphere at 80° C. The reaction mixture was cooled, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1) to give the title compound (0.21 g, yield 22%) as an oil.

Provenance & Evidence