Triethylamine → 4-Trifluoromethylphenyl alpha-fluoroacrylate

HRID 258326

Reaktionsgleichung

Reaktionsgleichung von HRID 258326
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:19][C:20](=[CH2:24])[C:21](Cl)=[O:22]>C(OCC)C>[F:19][C:20](=[CH2:24])[C:21]([O:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 678744-(Trifluoromethyl)phenolHCID 27833352-Fluoroacryloyl chloride

Produkt 1

HCID 140081564-Trifluoromethylphenyl alpha-fluoroacrylateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

16.2 g (0.1 mol) of 4-trifluoromethylphenol were dissolved in 80 ml of anhydrous diethyl ether, and 10.1 g (0.1 mol) of triethylamine were added in portions to the solution; 12 g (0.11 mol) of α-fluoroacryloyl chloride (obtained in accordance with example 1c) were then added dropwise, at a temperature of 10° C., with stirring, and in the course of 20 minutes, and the reaction mixture was stirred for a further 60 minutes at the same temperature. The solid formed was filtered off and washed with 20 ml of diethyl ether. The mixture of filtrate and wash solution was distilled, after adding 0.005 g of hydroquinone monomethyl ether. 19.5 g (83% of theory) of 4-trifluoromethylphenyl α-fluoroacrylate were obtained, boiling point 69° to 70° C. (under 3 mbar).

Aufarbeitung

  1. stirringin the course of 20 minutes, and the reaction mixture was stirred for a further 60 minutes at the same temperature
  2. customThe solid formed
  3. filtrationwas filtered off
  4. washwashed with 20 ml of diethyl ether
  5. additionThe mixture of filtrate
  6. washwash solution
  7. distillationwas distilled
  8. additionafter adding 0.005 g of hydroquinone monomethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-80f61fe3520b47059f5e5963bbdaf483
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05266668

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