Toluene → HCID 59866480, compound

Participants

Reaction Steps

A nitrogen flushed mixture of 1,3-dibromobenzene (18.63 g, 78.92 mmol), dibenzo{b,d}thiophen-4-ylboronic acid (6.0 g, 26.3 mmol), Pd(PPh3)4 (304 mg, 0.414 mmol), toluene (200 mL) and a slurry of K2CO3 (10.9 g, 78.92 mmol) in water (20 mL) were refluxed for 23 h. After the mixture cooled to room temperature the organic layer was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by vacuum distillation (Kugelrohr) followed by flash chromatography on silica (hexane:dichloromethane) to give 4-(3-bromophenyl)dibenzo[b,d]thiophene (3.5 g 39.2%).

Provenance & Evidence