Reacción #10367

Ecuación de reacción

2,3,4,5,6-pentafluorobenzoic acid

benzyl alcohol

1-[3-(Dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride

→

title compound

Rendimiento 77.3%

2,3,4,5,6-Pentafluorobenzoic acid benzyl ester

Rendimiento 77.3%

Disolventes

brine

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 24 hours
3. 3
   ExtracciónThe mixture is extracted with chloroform
4. 4
   Lavadothe organic phase washed with NaHCO3
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under vacuum

Procedimiento

A solution of 2,3,4,5,6-pentafluorobenzoic acid (15.25 g, 71.9 mmol), 4-dimethylaminopyridine (4.4 g, 36.0 mmol) and benzyl alcohol (7.4 mL, 71.5 mmol) in dichloromethane (150 mL) is cooled to 0° C. under an inert atmosphere. 1-[3-(Dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (16.7 g, 87.1 mmol) is added and the mixture stirred at 0° C. for 2 hours. The mixture is warmed to ambient temperature, stirred for 24 hours, and then poured into brine. The mixture is extracted with chloroform and the organic phase washed with NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to yield the title compound as a white solid (16.7 g). This material is used without further purification. 1H NMR (CDCl3): δ 7.49–7.27 (m, 5H), 5.40 (s, 2H).

Fuente