Fluorobenzene → 2-Bromo-1-(4-fluorophenyl)-2-methylpropan-1-one

HRID 918285Notes

Reaction equation

HRID 918285 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:12][C:13]([CH3:18])([CH3:17])[C:14](Br)=[O:15]>C(=S)=S>[Br:12][C:13]([CH3:18])([CH3:17])[C:14]([C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1)=[O:15]

Participants

5

Reactant 3

HCID 10008FluorobenzeneHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 131131752-Bromo-1-(4-fluorophenyl)-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
20 °C

Procedure

A slurry of 14 g. (0.105 mole) of anhydrous aluminum chloride in 14.4 g. (0.150 mole) of fluorobenzene and 24 ml. of carbon disulfide is cooled to 15°C. To it is added 23.8 g. (0.100 mole) of α-bromoisobutyryl bromide over 10-15 minutes at 15°-20°C. The reaction is stirred for 5 minutes at 20°C and then quenched on ice. The product is extracted into chloroform. The chloroform layer is washed with aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated to give 2-bromo-4'-fluoro-2-methylpropiophenone.

Workup

  1. additionTo it is added 23.8 g
  2. customquenched on ice
  3. extractionThe product is extracted into chloroform
  4. washThe chloroform layer is washed with aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1aaaab56c0f145c2b8bc7e56c6d87ab8
Source dataset
uspto-grants-1976_07
Patent number
US03970693

Reaction notes

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