O-Xylene → 2-Chloro-4,5-difluorobenzonitrile

HRID 129244

Reaktionsgleichung

Reaktionsgleichung von HRID 129244
[F-:1].[K+].CC(CC(O)CO)C.[Cl:11][C:12]1[CH:19]=[C:18](Cl)[C:17]([F:21])=[CH:16][C:13]=1[C:14]#[N:15].C1(C)C(C)=CC=CC=1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC>[Cl:11][C:12]1[CH:19]=[C:18]([F:1])[C:17]([F:21])=[CH:16][C:13]=1[C:14]#[N:15]

Komponenten

6

Edukt 4

HCID 7237O-XyleneHCID 911714-Methylpentane-1,2-diolHCID 522689Potassium FluorideHCID 27827532,4-Dichloro-5-fluorobenzonitrile

Produkt 1

HCID 40858492-Chloro-4,5-difluorobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 76564Tetrabutylphosphonium bromideKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a 100 ml flange flask fitted with a distillation bridge and anchor stirrer, 14.5 g (0.25 mol) of potassium fluoride, 4.8 g (0.007 mol) of trimethyl(ethoxypolyoxypropyl)ammonium chloride, 6.2 g (0.012 mol) of polyethylene glycol dimethyl ether 500 and 2.4 g (0.007 mol) of tetrabutylphosphonium bromide were introduced at 100° C. into the melt of 47.5 g (0.25 mol) of 2,4-dichloro-5-fluorobenzonitrile. Subsequently, 10 g (0.09 mol) of xylene were added and the reaction suspension was azeotropically dried by application of a vacuum of 20 mbar and heating to 130° C. After the xylene had been distilled off, the reaction suspension was heated to 140° C. and stirred for 8 hours at this temperature. Amount of 2-chloro-4,5-difluorobenzonitrile formed:

Aufarbeitung

  1. customthe reaction suspension was azeotropically dried by application of a vacuum of 20 mbar
  2. distillationAfter the xylene had been distilled off
  3. temperaturethe reaction suspension was heated to 140° C.

Quellen und Nachweise

ORD-Eintrag
ord-6f0eb02cbc95451ca753776a47119975
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466859

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