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

HRID 918288Notes

Reaction equation

HRID 918288 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[C:9]([CH3:11])=[CH2:10])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8](=[O:12])[CH:9]([CH3:11])[CH2:10]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 132782011-(4-Fluorophenyl)-2-methylprop-2-en-1-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
45 °C

Procedure

Fifty grams (0.30 moles) of 4'-fluoro-2-methylacrylophenone is added to a slurry of 60.1 g. (0.45 moles) of anhydrous aluminum chloride in 27 ml. of carbon disulfide at 20° to 25°C over 1 hour. The mixture is heated to 45°C over 1 hour and stirred at 45°C for 1 hour. The reaction is quenched in ice. The oily aqueous layer is extracted with 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. customThe reaction is quenched in ice
  2. extractionThe oily aqueous layer is extracted with toluene
  3. washThe toluene layer is washed with aqueous sodium hydroxide and water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2221a6f703c3476e91a5fa065146cc4a
Source dataset
uspto-grants-1976_07
Patent number
US03970693

Reaction notes

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