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

HRID 741686Notes

Reaction equation

HRID 741686 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)Cl.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:20])[CH:9]([Br:21])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

Product 1

HCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of the product of step 3 (40.5 g, 139 mmol) in CCl4 (500 mL) and CHCl3 (2 L) was added dropwise a solution of Br2 in CCl4 (50 mL). After addition was completed, the mixture was washed with saturated NaHCO3 (500 mL) and Na2S2O8 (2×250 mL). The pale yellow solution was dried over Na2SO4 and concentrated to dryness. The residue was stirred in 50 % EtO2 /hexane for 20 h and filtered to give 49 g of the title compound.

Workup

  1. additionAfter addition
  2. washthe mixture was washed with saturated NaHCO3 (500 mL) and Na2S2O8 (2×250 mL)
  3. dry with materialThe pale yellow solution was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. filtrationfiltered

Sources & evidence

ORD record
ord-932fe0462e21401da6c77504cfac146b
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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