Sulfuric Acid → 5-Fluoro-2-methylindan-1-one

HRID 267829Notes

Reaction equation

HRID 267829 reaction equation
CN(C)[CH2:3][CH:4]([CH3:14])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].S(=O)(=O)(O)O>>[F:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[C:5](=[O:6])[CH:4]([CH3:14])[CH2:3]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 215218873-(Dimethylamino)-1-(4-fluorophenyl)-2-methylpropan-1-one

Product 1

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

Conditions

Temperature
90 °C

Procedure

A mixture of 42 g. (0.20 mole) of 3-dimethylamino-4'-fluoro-2-methylpropiophenone and 100 ml. of concentrated sulfuric acid is warmed to 90°C over one hour and stirred at 90°C for two hours. The reaction is cooled and quenched in ice and the product 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. additionA mixture of 42 g
  2. temperatureThe reaction is cooled
  3. customquenched in ice
  4. extractionthe product extracted into toluene
  5. washThe toluene layer is washed with aqueous sodium hydroxide and water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50c7515c35324b5c9820dbf91855b0db
Source dataset
uspto-grants-1976_03
Patent number
US03944600

Reaction notes

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