Bromine → 2-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

HRID 433919

Reaction equation

HRID 433919 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Br:21]Br>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Br:21][CH:9]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=1)[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:20]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

Product 1

HCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanoneYield 75.4%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6212ChloroformSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-2-(4-methylsulfonyl phenyl)ethanone (14.6 g, 50 mmol) in 210 mL of chloroform and 826 mL of CCl4. A solution of 8.0 g (50 mmol) of bromine in CCl4 was added dropwise to the mixture. When the loss of the bromine colour was complete, the organic layer was washed with 5% aqueous sodium bicarbonate solution and with brine. It was dried over anhydrous sodium sulfate. The drying agent was filtered, and the filtrate concentrated in vacuum to give 14.0 g (70%) of the desired product as a solid.

Workup

  1. washthe organic layer was washed with 5% aqueous sodium bicarbonate solution and with brine
  2. dry with materialIt was dried over anhydrous sodium sulfate
  3. filtrationThe drying agent was filtered
  4. concentrationthe filtrate concentrated in vacuum

Sources & evidence

ORD record
ord-84880694e21f4168b30407757433a720
Source dataset
uspto-grants-2003_12
Patent number
US06670365B1

Linked notes

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