Reaction #1726706

Reaction equation

2-(N-Boc-amino)-3-phenyl-thiophene

N-chlorosuccinimide

→

2-(N-Boc-amino)-5-chloro-3-phenyl-thiophene

Yield 66.6%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherat 0° C.
2. 2
   Washwashed with water
3. 3
   Concentrationthe organic phase concentrated in vacuo

Procedure

To 2-(N-Boc-amino)-3-phenyl-thiophene (89 mg, 0.32 mmol) in dichloromethane (4 ml) at 0° C. was slowly added N-chlorosuccinimide (48 mg, 0.36 mmol), and the mixture allowed warm to ambient temperature for 16 hr. The mixture was diluted with dichloromethane, washed with water, and the organic phase concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 2-(N-Boc-amino)-5-chloro-3-phenyl-thiophene (66 mg, 66%).

Source