Reacción #567111

Ecuación de reacción

11-bromo-1-undecanol

3,5-dinitrobenzoyl chloride

Pyridine

→

3,5-Dinitrobenzoic acid 11-bromoundecyl ester

Rendimiento 90.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 4.5 hours at 0° C. the reaction mixture was partitioned between dichloromethane and water
2. 2
   Lavadothe organic phase was washed repeatedly with water
3. 3
   Secadodried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated by rotary evaporation

Procedimiento

11.4 g (45.4 mmol) 11-bromo-1-undecanol, 11.0 g (47.7 mmol) 3,5-dinitrobenzoyl chloride, 54 mg 4-dimethylaminopyridine were dissolved in 94 ml dichloromethane. The solution was subsequently cooled to 0° C. and then 18.3 ml (227 mmol) Pyridine was added dropwise, in the course of 25 minutes. After 4.5 hours at 0° C. the reaction mixture was partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using Toluene yielded 18.1 g (90%) 3,5-Dinitrobenzoic acid 11-bromoundecyl ester as yellow powder.

Fuente