N-bromobutanimide → HCID 58521981, compound

HRID 2390259Notes

Reaction equation

HRID 2390259 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH3:11])(=[O:10])=[O:9].[Br:12]N1C(=O)CCC1=O>OS(O)(=O)=O>[Br:12][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[C:3]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20080599HCID 20080599, compound2×

Product 1

HCID 58521981HCID 58521981, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of 1-iodo-2-(methylsulfonyl)benzene (Intermediate 201; 1.45 g; 5.14 mmol) in conc. H2SO4 (4 mL) was treated with N-bromosuccinimide (1.01 g; 5.65 mmol) and the resulting mixture was stirred for 4 h. The reaction mixture was carefully poured on crushed ice and extracted with EtOAc. The organic phase was washed twice with NaOH 0.1 N and brine, dried over MgSO4, filtered and concentrated to dryness affording the title compound as a white solid (1.6 g, 86%).

Workup

  1. additionThe reaction mixture was carefully poured
  2. customon crushed ice
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed twice with NaOH 0.1 N and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4e3850951c4040798a9b06be4a707e60
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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