Aluminum(III) Chloride → 5-Fluoro-1-indanone

HRID 375598

Reaction equation

HRID 375598 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH2:5][CH2:6][C:7](Cl)=[O:8].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[F:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:7](=[O:8])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 189935013-(3-Fluorophenyl)propanoyl chloride

Product 1

HCID 1365375-Fluoro-1-indanoneYield 16.1%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

A solution of 3-fluorodihydrocinnamoyl chloride (15.4 g) in carbon disulfide (78 ml) was added dropwise to a cold (-5° C.) mixture of aluminium chloride (13.9 g) in carbon disulfide (300 ml) for 30 minutes. During this time and for 30 minutes the mixture was allowed to warm to room temperature (1 hr), then it was heated to reflux (1 hr) and finally the volatiles were removed by distillation under reduced pressure. The residue was dissolved in methylene chloride (400 ml) and washed successively with 10% aqueous sodium hydroxide and water. After drying (magnesium sulfate) and solvent removal in vacuo, 5-fluoroindanone (2 g) was isolated by recrystallisation from hexane.

Workup

  1. temperatureit was heated
  2. temperatureto reflux (1 hr)
  3. customfinally the volatiles were removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in methylene chloride (400 ml)
  5. washwashed successively with 10% aqueous sodium hydroxide and water
  6. customAfter drying
  7. custom(magnesium sulfate) and solvent removal in vacuo

Sources & evidence

ORD record
ord-e4074e4510fa425b95af15b30757d78f
Source dataset
uspto-grants-1996_01
Patent number
US05486541

Linked notes

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