Lithium Bromide → 2-Difluoromethoxy-6-nitrobenzonitrile

HRID 39220

反応式

HRID 39220 の反応式
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]

参加物

6

反応物 3

HCID 82050Lithium BromideHCID 581007662-Bromo-1-(difluoromethoxy)-3-nitrobenzeneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 581007642-Difluoromethoxy-6-nitrobenzonitrile収率 84.6%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
200 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47972b48f6ac4d3da12438dc0306f2c1
出典データセット
uspto-grants-2013_09
特許番号
US08524896B2

関連ノート

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