Sodium Carbonate → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-dichlorobis(triphenyl-phosphine)palladium (ii) (0.138 g, 0.196 mmol), phenylboronic acid (0.717 g, 5.88 mmol), 1-(3-bromobenzo[b]thiophen-2-yl)ethanone (0.50 g, 1.960 mmol) and 2.0 N aqueous sodium carbonate (2.94 mL, 5.88 mmol) in Toluene (10 mL) was purged with nitrogen and heated to 110° C. overnight. After 16 h, the reaction mixture was partitioned between EtOAc and water. The organic layer was stirred over MgSO4, filtered and concentrated under reduced pressure to give a red oil. The product was purified by column chromatography on a silica gel column using 20 to 40% gradient of EtOAc in hexane as eluent to give 1-(3-phenylbenzo[b]thiophen-2-yl)ethanone a colorless oil: 1H NMR (400 MHz, CDCl3) δ 2.12 (s, 3H) 7.30-7.35 (m, 1H) 7.38-7.42 (m, 2H) 7.42-7.49 (m, 2H) 7.52-7.58 (m, 3H) 7.87 (d, J=8.2 Hz, 1H); LC-MS (ESI)] m/z 253.1 [M+H]+.

Provenance & Evidence