Fluorobenzene → 1-Bromo-2-fluoro-4-[(4-fluorophenyl)sulfonyl]benzene

HRID 1963675Notes

Reaction equation

HRID 1963675 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

3

Reactant 2

HCID 10008FluorobenzeneHCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 684345101-Bromo-2-fluoro-4-[(4-fluorophenyl)sulfonyl]benzene

Procedure

Ferric chloride (0.5 g) was added to a mixture of 4-bromo-3-fluoro-benzenesulfonyl chloride (2.5 g) and fluorobenzene (3 ml) and then stirred at reflux for 18 hours. The flask was cooled to room temperature and the residue was partitioned between aqueous NaHCO3 and DCM. The DCM layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was recrystallised from ethanol to give buff coloured crystals.

Workup

  1. temperatureat reflux for 18 hours
  2. customthe residue was partitioned between aqueous NaHCO3 and DCM
  3. washThe DCM layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallised from ethanol
  7. customto give buff coloured crystals

Sources & evidence

ORD record
ord-529fc026d5114cca887b0c1e99258983
Source dataset
uspto-grants-2013_04
Patent number
US08415394B2

Reaction notes

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