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

HRID 362806

Reaction equation

HRID 362806 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 15194646-Fluoro-1-indanoneYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.;

Workup

  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

Sources & evidence

ORD record
ord-eeb2a8b5c66a43359f690b7688ecdf85
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Linked notes

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