Reacción #1532

Ecuación de reacción

ammonium chloride

n-butyl lithium

N-t-butyl-3-bromo-2-thiophenesulfonamide

ethyl fluoroacetate

→

pure title compound

Rendimiento 72.0%

N-t-butyl-3-(fluoroacetyl)-2-thiophenesulfonamide

Rendimiento 72.0%

Disolventes

ethylacetate

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe temperature of the mixture was raised slowly to -20° C.
2. 2
   Temperaturaagain cooled to -78° C
3. 3
   TemperaturaThe temperature of the mixture was raised again slowly to -20° C.
4. 4
   Otroto separate the organic layer
5. 5
   SecadoThe extracted organic layer was dried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

2.98 g (0.0mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide was dissolved in 50mi of dry tetrahydrofuran and the mixture was cooled to -78° C. under nitrogen gas. To the reaction solution was slowly added dropwise 8.4 ml of n-butyl lithium (2.5N) and then the temperature of the mixture was raised slowly to -20° C. and again cooled to -78° C. 1.2 g (0.011 mole) of ethyl fluoroacetate was added slowly to the reaction mixture. The temperature of the mixture was raised again slowly to -20° C. and then the mixture was stirred for 10 minutes. To the reaction mixture was added 100 ml of 5% aqueous ammonium chloride solution, and then added 100 ml of ethylacetate to separate the organic layer. The extracted organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjeced to column chromatography on silica gel to obtain 2.0 g (Yield: 72%) of the pure title compound as a liquid.

Fuente