Реакция #361963

Уравнение реакции

HCl

4-nitrophenol

3,4,4-trifluoro-3-butenoyl chloride

triethylamine

→

product

Выход 92.1%

3,4,4-trifluoro-3-butenoic acid, 4-nitrophenyl ester

Выход 92.1%

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture is stirred at -78° C. for 10 min
2. 2
   Другоеto reach room temperature
3. 3
   ПромывкаThe organic layer is successively washed with water, 5% sodium bicarbonate, brine
4. 4
   Другоеdried
5. 5
   ДругоеThe dark brown residue obtained
6. 6
   Другоеafter evaporation of the solvent
7. 7
   Другоеwas purified

Методика

A solution of 4-nitrophenol (1.10 g, 0.0079 mole) and 3,4,4-trifluoro-3-butenoyl chloride (1.85 g, 0.0116 mole) in dry ether (15 mL) is treated dropwise with triethylamine (1.01 g, 0.01 mole) at -78° C. with stirring. The mixture is stirred at -78° C. for 10 min and allowed to reach room temperature. The reaction mixture is diluted with ether (20 mL), stirred with 15 mL of 2N HCl. The organic layer is successively washed with water, 5% sodium bicarbonate, brine, and dried. The dark brown residue obtained after evaporation of the solvent was purified by passing through a short column of silica gel to give 1.9 g of the product as a brown solid, a 91% yield. m.p. 58°-62° C.

Источник