Sodium Carbonate → 2-(3-Methoxyphenyl)-6,7-dihydro-5H-benzo[b]thiophen-4-one

Participants

Reaction Steps

To 2-bromo-6,7-dihydro-5H-benzo[b]thiophen-4-one (5 g, 21.74 mmol) was successively added 3-methoxyphenol boronic acid (3.63 g, 23.92 mmol), 2M Na2CO3(aq) (43.5 mL, 86.98 mmol), Pd(PPh3)4 (251 mg, 0.22 mmol), 3:4 EtOH/H2O (37.5 mL) and DME (62.5 mL). The reaction mixture was degassed and heated to reflux for 12 hours. EtOAc (250 mL) was added and the crude reaction mixture was washed with water (2×100 mL). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with EtOAc:hexanes (20:80) to give the title compound as an off-white solid in 95% yield. MS (ES+) 259. δH (d6 DMSO) 2.13 (2H, quint.), 2.50 (2H, m), 3.05 (2H, t), 3.81 (3H, s), 6.91 (1H, m), 7.20-7.22 (2H, m), 7.34 (1H, m), 7.67 (1H, s).

Provenance & Evidence