Boron trifluoride → 5-Bromo-3-methyl-2-(4-propylbenzyl)thiophene

Participants

Reaction Steps

To a solution of (5-bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone (45, 0.95 g, 2.95 mmol) in DCM (9.4 mL) and ACN (9.4 mL) was added triethylsilane (1.42 mL, 8.85 mmol) followed by BF3 etherate (1.11 mL, 8.85 mmol) under nitrogen atmosphere at 0° C. The reaction mixture was allowed warmed to room temperature and stirred for 16 hours. The mixture was poured into a saturated K2CO3 solution (50 mL) and extracted with EtOAc (100 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide 5-bromo-3-methyl-2-(4-propylbenzyl)thiophene (46, 0.86 g, 2.77 mmol, 94%).

Provenance & Evidence