تفاعل #10367

معادلة التفاعل

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

benzyl alcohol

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

→

title compound

المردود 77.3%

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

المردود 77.3%

المذيبات

brine

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 24 hours
3. 3
   استخلاصThe mixture is extracted with chloroform
4. 4
   غسيلthe organic phase washed with NaHCO3
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under vacuum

الإجراء التجريبي

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).

المصدر