Reacción #340288

Ecuación de reacción

H2O

Sodium hydride

trimethylsulfoxonium iodide

(E)-3-(2-bromo-5-fluorophenyl)-N-methoxy-N-methylacrylamide

→

title compound

2-(2-Bromo-5-fluorophenyl)-N-methoxy-N -methylcyclopropane-carboxamide

Disolventes

DMSO

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at 25° C. for 12 h
2. 2
   Extracciónthe title compound was extracted
3. 3
   SecadoThe organic layer was dried over sodium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   OtroPurification by flash column chromatography (33% EtOAc/hexane)

Procedimiento

Sodium hydride (60%, 122 mg, 3.05 mmol, Aldrich) was added to a suspension of trimethylsulfoxonium iodide (671 mg, 3.05 mmol, Aldrich) in DMSO (6 mL). The mixture was stirred at 25° C. for 30 min, and (E)-3-(2-bromo-5-fluorophenyl)-N-methoxy-N-methylacrylamide was added as a solution in DMSO (3 mL). The mixture was stirred at 25° C. for 12 h, then transferred to a separatory funnel with H2O (40 mL), and the title compound was extracted using 75% ether/hexane (3×40 mL). The organic layer was dried over sodium sulfate and concentrated. Purification by flash column chromatography (33% EtOAc/hexane) afforded the title compound as a colorless oil. MS m/z: 302 and 304 (M+1).

Fuente