Lithium Bromide → 2-Difluoromethoxy-6-nitrobenzonitrile

HRID 39220

반응식

HRID 39220 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 581007642-Difluoromethoxy-6-nitrobenzonitrile수율 84.6%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
200 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47972b48f6ac4d3da12438dc0306f2c1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524896B2

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