Benzeneacetic acid, 4-bromo- → HCID 13773530, compound

Participants

Reaction Steps

A mixture of 4-bromophenylacetic acid (1.08 g, 5 mmol), 3-thiopheneboronic acid (0.7 g, 5.5 mmol), NaHCO3 (1.68 g, 20 mmol), and dichlorobis(triphenylphosphine)palladium (0.35 g, 0.5 mmol) in DME-water (21 mL-7 mL) was heated at reflux temperature for 2 hours under nitrogen. After cooling, the reaction mixture was partitioned between Et2O (80 mL) and saturated aqueous NaHCO3 (30 mL). The organic layer was washed with saturated aqueous NaHCO3 (30 mL) again. The combined aqueous layer was acidified with 2N HCl solution and the whole extracted with CH2Cl2 (50 mL×3). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2) eluting with ethyl acetate/hexane (1/1) to give the subtitle compound (0.56 g, 51% yield).

Provenance & Evidence