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

HRID 2390136Notes

Reaction equation

HRID 2390136 reaction equation
[CH3:1][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.[Br:14]N1C(=O)CCC1=O.S(=O)(=O)(O)O>BrN1C(=O)CCC1=O>[Br:14][C:3]1[CH:4]=[C:5]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 2843351-Methyl-4-(propylsulfonyl)benzene2×

Product 1

HCID 585220912-Bromo-1-methyl-4-(propylsulfonyl)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 67184N-bromobutanimideCatalyst

Procedure

A finely ground mixture of 1-methyl-4-(propylsulfonyl)benzene (Intermediate 36; 24.80 g; 0.13 mol) and N-bromosuccinimide (26.8 g; 0.15 mol) was treated with conc. sulfuric acid (115 ml; 2.15 mol). The reaction mixture was stirred for 16 h then treated with a further portion of N-bromosuccinimide (1.33 g; 0.01 mol). The reaction solution was stirred 1 h then carefully poured into 800 mL of crushed ice. The aqueous solution was extracted with 400 mL of AcOEt. The layers were separated and the organic phase was washed first with ca. 300 mL of brine, then twice with a 1N solution of NaOH in water and twice with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound (29.3 g, 85%) as a brown oil which solidified upon standing.

Workup

  1. stirringThe reaction solution was stirred 1 h
  2. extractionThe aqueous solution was extracted with 400 mL of AcOEt
  3. customThe layers were separated
  4. washthe organic phase was washed first with ca. 300 mL of brine
  5. customThe organic phase was dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cafdb2ec1fdc437c880a6f67361fdd2b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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