Sulfuric Acid → 2-Bromo-1-fluoro-4-(propylsulfonyl)benzene

HRID 2390190Notes

Reaction equation

HRID 2390190 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[Br:19]N1C(=O)CCC1=O>>[Br:19][C:7]1[CH:6]=[C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 142895251-Fluoro-4-(propylsulfonyl)benzene2×

Product 1

HCID 585220712-Bromo-1-fluoro-4-(propylsulfonyl)benzene

Procedure

A suspension of 1-fluoro-4-(propylsulfonyl)benzene (Intermediate 105; 1.00 g; 4.94 mmol) in conc. sulfuric acid (3.97 ml; 74.2 mmol) was treated with N-bromosuccinimide (968 mg; 5.44 mmol) and stirred at RT for 6 hours. The reaction mixture was carefully poured on crushed ice, extracted with AcOEt and the organic phase was washed with a 0.1 N solution of NaOH in water twice, then with brine twice. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give a residue, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound.

Workup

  1. additionThe reaction mixture was carefully poured
  2. customon crushed ice
  3. extractionextracted with AcOEt
  4. washthe organic phase was washed with a 0.1 N solution of NaOH in water twice
  5. customThe organic phase was dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue, which
  9. customwas purified by flash column chromatography (silica)
  10. washeluting with cyclohexane containing
  11. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-ab68648557ba44d8ae7aa117c764dab5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…