Reaktion #10367

Reaktionsgleichung

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

benzyl alcohol

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

→

title compound

Ausbeute 77.3%

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

Ausbeute 77.3%

Lösungsmittel

brine

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 24 hours
3. 3
   ExtraktionThe mixture is extracted with chloroform
4. 4
   Waschenthe organic phase washed with NaHCO3
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under vacuum

Vorschrift

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).

Quelle