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

HRID 358807

반응식

HRID 358807 반응식
[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]

참가 물질

5

반응물 2

HCID 753784-Bromo-2-fluoroanisoleHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 27745483-Fluoro-4-methoxybenzonitrile수율 78%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-d3fc8bc045b6442b88e625d098ce7d2f
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04997942

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