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

HRID 358807

反応式

HRID 358807 の反応式
[F:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Cu](C#N)[C:12]#[N:13]>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:9][CH3:10])[C:12]#[N:13]

参加物

5

反応物 2

HCID 753784-Bromo-2-fluoroanisoleHCID 178418260HCID 178418260、化合物

生成物 1

HCID 27745483-Fluoro-4-methoxybenzonitrile収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

20 g of the 2-fluoro-4-bromoanisole thus obtained and 9.8 g of copper cyanide were dissolved in 100 ml of dimethyl formamide and heated under reflux for ten hours. To the reaction mixture, was added an aqueous solution of 20 g of ferric chloride in 100 ml of water. The reaction mixture was allowed to cool to room temperature and the reaction product was extracted with toluene. The organic layer was successively washed with water, a saturated aqueous solution of sodium carbonate and a saturated aqueous solution of common salt. Then the organic layer was separated. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate 10:1) and further recrystallized from ethanol. Thus 10.0 g of 3-fluoro-4-methoxybenzonitrile was obtained. Yield: 68%.

後処理

  1. temperatureheated
  2. temperatureunder reflux for ten hours
  3. extractionthe reaction product was extracted with toluene
  4. washThe organic layer was successively washed with water
  5. customThen the organic layer was separated
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate 10:1)
  9. customfurther recrystallized from ethanol

出典と根拠

ORDレコード
ord-d3fc8bc045b6442b88e625d098ce7d2f
出典データセット
uspto-grants-1991_03
特許番号
US04997942

関連ノート

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