Aluminum(III) Chloride → 5-Fluoro-2-methylindan-1-one

HRID 918286Notes

Reaction equation

HRID 918286 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Br[C:6]([CH3:17])([CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8]>C(=S)=S>[F:15][C:12]1[CH:11]=[C:10]2[C:9](=[CH:14][CH:13]=1)[C:7](=[O:8])[CH:6]([CH3:17])[CH2:16]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 131131752-Bromo-1-(4-fluorophenyl)-2-methylpropan-1-one

Product 1

HCID 30162575-Fluoro-2-methylindan-1-one

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
50 °C

Procedure

To a slurry of 120.2 g. (0.90 mole) of anhydrous aluminum chloride in 54 ml. of carbon disulfide is added 122.6 g. (0.50 mole) of 2-bromo-4'-fluoro-2-methylpropiophenone at 15° to 20°C over 1 hour. The mixture is warmed to 50°C over 1 hour, stirred at 50°C for 3 hours and quenched in ice. The product is extracted into toluene. The toluene layer is washed with aqueous sodium hydroxide and water and concentrated in vacuo to give 5-fluoro-2-methyl-1-indanone.

Workup

  1. customquenched in ice
  2. extractionThe product is extracted into toluene
  3. washThe toluene layer is washed with aqueous sodium hydroxide and water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49fe12b1b1f14933a143cba92edc8773
Source dataset
uspto-grants-1976_07
Patent number
US03970693

Reaction notes

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