4-Fluorobenzyl chloride → 1-[5-[(4-Fluorophenyl)methyl]-2-furanyl]ethanone

HRID 2307534노트

반응식

HRID 2307534 반응식
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[C:1]([C:4]1[O:5][C:6]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([F:9])=[CH:11][CH:12]=2)=[CH:7][CH:8]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 96024-Fluorobenzyl chlorideHCID 145052-Acetylfuran

생성물 1

HCID 101306401-[5-[(4-Fluorophenyl)methyl]-2-furanyl]ethanone수율 42%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 19.71 g (0.18 mol) of 2-acetylfuran in 120 ml of methylene chloride were added 42.9 ml (2.0 eq) of 4-fluorobenzylchloride and 36.6 g (1.5 eq) of zinc chloride. The mixture was refluxed for 12 hours. The precipitated crystal was filtered and washed with methylene chloride. The obtained solid was dissolved in water and extracted with ethylacetate. The organic layer was washed with water and a diluted aqueous solution of sodium hydrogencarbonate and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from n-hexane to give 16.4 g of 2-acetyl-5-(4-fluorobenzyl)furan. Yield: 42%. Mp: 27-29° C.

후처리

  1. temperatureThe mixture was refluxed for 12 hours
  2. filtrationThe precipitated crystal was filtered
  3. washwashed with methylene chloride
  4. dissolutionThe obtained solid was dissolved in water
  5. extractionextracted with ethylacetate
  6. washThe organic layer was washed with water
  7. dry with materiala diluted aqueous solution of sodium hydrogencarbonate and dried over sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was recrystallized from n-hexane

출처 및 근거

ORD 기록
ord-9cf9c6656e084b20b4d3fc1af9d964fe
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831177B1

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