Lithium Bromide → 2-Difluoromethoxy-6-nitrobenzonitrile

HRID 39220

Reaktionsgleichung

Reaktionsgleichung von HRID 39220
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH:12]([F:14])[F:13].[C:15]([Cu])#[N:16].[Li+].[Br-]>O1CCCC1.C1(C)C=CC=CC=1>[F:13][CH:12]([F:14])[O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[C:15]#[N:16]

Komponenten

6

Edukt 3

HCID 82050Lithium BromideHCID 581007662-Bromo-1-(difluoromethoxy)-3-nitrobenzeneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 581007642-Difluoromethoxy-6-nitrobenzonitrileAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 2-bromo-1-difluoromethoxy-3-nitro-benzene (1 g, 3.7 mmol), CuCN (0.40 g, 4.5 mmol) and LiBr (0.32 g, 3.7 mmol) in tetrahydrofuran (10 ml) are heated in a microwave oven at 200° C. for 40 minutes. The reaction mixture is cooled to ambient temperature, diluted with toluene and washed with aqueous sodium bromide (1M) and aqueous sodium hydrogen sulfite (saturated). The organic phase is dried over sodium sulfate and concentrated. The residue is purified by HPLC to give 2-difluoromethoxy-6-nitrobenzonitrile (0.67 g, 84% yield). 1H-NMR (CDCl3, 400 MHz): 8.20 (d, 1H), 7.85 (t, 1H), 7.75 (d, 1H), 6.75 (t, 1H) ppm.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to ambient temperature
  2. washwashed with aqueous sodium bromide (1M) and aqueous sodium hydrogen sulfite (saturated)
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-47972b48f6ac4d3da12438dc0306f2c1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524896B2

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