Hydrochloric Acid → 3,4,4-Trifluoro-3-butenoic acid, 4-nitrophenyl ester

HRID 54733

Reaktionsgleichung

Reaktionsgleichung von HRID 54733
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:11][C:12](=[C:17]([F:19])[F:18])[CH2:13][C:14](Cl)=[O:15].C(N(CC)CC)C.Cl>CCOCC>[F:11][C:12](=[C:17]([F:19])[F:18])[CH2:13][C:14]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 9804-NitrophenolHCID 8471TriethylamineHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Produkt 1

HCID 152391903,4,4-Trifluoro-3-butenoic acid, 4-nitrophenyl esterAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringThe mixture is stirred at -78° C. for 10 min
  2. customto reach room temperature
  3. washThe organic layer is successively washed with water, 5% sodium bicarbonate, brine
  4. customdried
  5. customThe dark brown residue obtained
  6. customafter evaporation of the solvent
  7. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-760aa76627d84edfb1a7dfe8d27792cc
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623084

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