Reaktion #83011

Reaktionsgleichung

HCl

4-nitrophenol

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

triethylamine

→

product

Ausbeute 92.1%

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

Ausbeute 92.1%

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred at -78° C. for 10 min
2. 2
   Sonstigeto reach room temperature
3. 3
   WaschenThe organic layer is successively washed with water, 5% sodium bicarbonate, brine
4. 4
   Sonstigedried
5. 5
   SonstigeThe dark brown residue obtained
6. 6
   Sonstigeafter evaporation of the solvent
7. 7
   Sonstigewas purified

Vorschrift

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 2 N 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.

Quelle