Triethylamine → 2-(4-Chlorophenyl)-ethin-1-yl 2,2-difluoro-1-methyl-cycloprop-1-yl ketone

HRID 248222

Reaktionsgleichung

Reaktionsgleichung von HRID 248222
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][C:18]1([C:23](Cl)=[O:24])[CH2:20][C:19]1([F:22])[F:21]>[Cu]Br.C1(C)C=CC=CC=1>[F:21][C:19]1([F:22])[CH2:20][C:18]1([C:23]([C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:24])[CH3:17]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 146952322,2-Difluoro-1-methylcyclopropane-1-carbonyl chloride

Produkt 1

HCID 146952462-(4-Chlorophenyl)-ethin-1-yl 2,2-difluoro-1-methyl-cycloprop-1-yl ketoneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

3.7 g (0.1 mol) of p-chlorophenyl-acetylene are added to a mixture of 10.1 g (0.1 mol) of triethylamine, 1.4 g (0.01 mol) of copper(I) bromide and 55 ml of toluene, and the mixture is stirred for 30 minutes at room temperature under argon. After the reaction mixture has been heated to 55° C., 15.5 g (0.1 mol) of 1-methyl-2,2-difluoro-cyclopropanecarbonyl chloride are added dropwise. After this, the mixture is stirred for 8 hours at 90° C., and then cooled and filtered. The filtrate is washed in succession with dilute aqueous hydrochloric acid and water and concentrated under reduced pressure. 19.2 g of a dark oil remain, which is distilled using a bulb tube. At 0.1 mbar and a jacket temperature of 120° C., a yellow oil passes over which solidifies on standing. 8.4 g (33% of theory) of 2-(4-chlorophenyl)-ethin-1-yl 2,2-difluoro-1-methylcycloprop-1-yl ketone of melting point 67°-68° C. are obtained. ##STR65##

Aufarbeitung

  1. temperatureAfter the reaction mixture has been heated to 55° C.
  2. stirringAfter this, the mixture is stirred for 8 hours at 90° C.
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe filtrate is washed in succession with dilute aqueous hydrochloric acid and water
  6. concentrationconcentrated under reduced pressure
  7. distillationwhich is distilled
  8. customa jacket temperature of 120° C.

Quellen und Nachweise

ORD-Eintrag
ord-31c0db8e18444cf1827d024bb070f7fd
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208388

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