N-Methyl-N-nitrosourea → Methyl 4-cyclopropyl-2,3,5,6-tetrafluorobenzoate

HRID 981265

Reaktionsgleichung

Reaktionsgleichung von HRID 981265
[F:1][C:2]1[C:11]([F:12])=[C:10]([CH:13]=[CH2:14])[C:9]([F:15])=[C:8]([F:16])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+](=[CH2:19])=[N-].C(OCC)C.CN(N=O)C(N)=O>C(OCC)C.C1(C)C(C)=CC=CC=1>[CH:13]1([C:10]2[C:11]([F:12])=[C:2]([F:1])[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:8]([F:16])[C:9]=2[F:15])[CH2:19][CH2:14]1

Komponenten

6

Edukt 3

HCID 12699N-Methyl-N-nitrosoureaHCID 15136253Methyl 2,3,5,6-tetrafluoro-4-vinylbenzoateHCID 21186548Diazomethane diethylether

Produkt 1

HCID 15136255Methyl 4-cyclopropyl-2,3,5,6-tetrafluorobenzoateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

In 10 ml of diethyl ether was dissolved 2.0 g of methyl 2,3,5,6-tetrafluoro-4-vinylbenzoate. To the resulting solution was added, with ice-cooling, a diazomethane-diethyl ether solution prepared from 3.0 g of N-methyl-N-nitrosourea. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was dissolved in 15 ml of xylene and the resulting solution was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain 2.1 g (yield: 99.1%) of methyl 4-cyclopropyl-2,3,5,6-tetrafluorobenzoate.

Aufarbeitung

  1. additionTo the resulting solution was added, with ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue obtained
  5. temperaturethe resulting solution was refluxed for 1 hour
  6. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b8ebed55f0cf475f9f7db15b818bd6ba
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990508

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