Sulfuric Acid → HCID 58522010, compound

HRID 2390216Notes

Reaction equation

HRID 2390216 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[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]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 7993014-fluoro-N,N-dimethylbenzenesulfonamide

Product 1

HCID 58522010HCID 58522010, compoundYield 82%

Procedure

A solution of 4-fluoro-N,N-dimethylbenzenesulfonamide (1.80 g; 8.86 mmol) in conc. sulfuric acid (7 ml; 130 mmol) was treated with N-bromosuccinimide (1 730 mg; 9.74 mmol) and stirred at RT for 3 h. 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 the title compound as a white solid (2.04 g, 82%).

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

Sources & evidence

ORD record
ord-7beaa1bc7d274309934cdfb3054616c8
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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