Reacción #1726706

ord-cba25e849d204f5f8a3ba379e1775efe

Ecuación de reacción

CC(C)(C)OC(=O)Nc1sccc1-c1ccccc1
2-(N-Boc-amino)-3-phenyl-thiophene
O=C1CCC(=O)N1Cl
N-chlorosuccinimide
CC(C)(C)OC(=O)Nc1sc(Cl)cc1-c1ccccc1
2-(N-Boc-amino)-5-chloro-3-phenyl-thiophene
Rendimiento 66.6%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroat 0° C.
  2. 2
    Lavadowashed with water
  3. 3
    Concentraciónthe organic phase concentrated in vacuo

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08110568B2uspto-grants-2012_02