4-Bromo-2-fluoroanisole → 3-Fluoro-4-methoxybenzonitrile

HRID 626129

反応式

HRID 626129 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([F:10])[CH:3]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.O>[F:10][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[C:11]#[N:12]

参加物

5

反応物 2

HCID 753784-Bromo-2-fluoroanisoleHCID 178418546HCID 178418546、化合物

生成物 1

HCID 27745483-Fluoro-4-methoxybenzonitrile収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-bromo-2-fluoro-1-methoxybenzene (30.0 g, 146 mmol) and CuCN (15.6 g, 174 mmol) in dry DMF (45 mL) was stirred at 120° C. overnight. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The extract was washed with water and brine, dried, and concentrated to give 20.0 g (91% yield) of the product as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.44 (dd, J=8.8 Hz, 2.0 Hz, 1H), 7.36 (dd, J=10.8 Hz, 2.0 Hz, 1H), 7.02 (dd, J=8.8 Hz, 8.4 Hz, 1H), 3.96 (s, 3H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. customdried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-06b96f53ce9c43e193786538c1a136cc
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

関連ノート

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