N-bromobutanimide → tert-Butyl (2-bromothiophen-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

According to the method described in WO2005070916, A boiling solution of tert-Butyl-N-(thiophen-3-yl)carbamate (5.32 g, 26.70 mmol) in dichloromethane (260 ml) was treated portionwise with N-bromo-succinimide (4.73 g, 26.70 mmol) under vigorous stirring. After addition was complete, the heating bath temperature was raised to 65° C. and maintained for 20 minutes before allowing the reaction to cool to room temperature. The reaction mixture was washed with water, dried (MgSO4), filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc) gave a clear oil which crystallized on standing (7.24 g, 97%).

Provenance & Evidence