Aluminum(III) Chloride → 6-Fluoro-1-indanone

HRID 362806

반응식

HRID 362806 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](Cl)=[O:11])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:8][CH2:9][C:10]2=[O:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 219642583-(4-Fluorophenyl)propionyl chloride

생성물 1

HCID 15194646-Fluoro-1-indanone수율 95.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3-(4-fluorophenyl)propionyl chloride (287.6 g, 1.5 mol) in dichloromethane (1.4 L) was added dropwise during 3 h to an ice-cold, mechanically stirred suspension of aluminum chloride (226.0 g, 1.7 mol, Aldrich) in dichloromethane (2.2 L) under nitrogen. The resulting yellowish-black solution was refluxed for 5 h and allowed to cool to room temperature. The solution was washed successively with water (2 L), 1N sodium hydroxide (2 L), water (2 L) and brine (2 L). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to a tan solid (229.1 g, 99%). The solid was recrystallized from dichloromethane-hexane to give 215.7 g (93%) of 6-fluoro-1-indanone as off-white crystals, m.p., 57°-59° C.;

후처리

  1. temperatureThe resulting yellowish-black solution was refluxed for 5 h
  2. washThe solution was washed successively with water (2 L), 1N sodium hydroxide (2 L), water (2 L) and brine (2 L)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a tan solid (229.1 g, 99%)
  6. customThe solid was recrystallized from dichloromethane-hexane

출처 및 근거

ORD 기록
ord-eeb2a8b5c66a43359f690b7688ecdf85
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872118

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