Реакция #10367

Уравнение реакции

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

benzyl alcohol

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

→

title compound

Выход 77.3%

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

Выход 77.3%

Растворители

brine

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe mixture is warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 24 hours
3. 3
   ЭкстракцияThe mixture is extracted with chloroform
4. 4
   Промывкаthe organic phase washed with NaHCO3
5. 5
   Сушкаdried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under vacuum

Методика

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).

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