P-Toluenesulfonamide → 3-Bromo-4-methylbenzene-1-sulfonamide

HRID 2357687Notes

Reaction equation

HRID 2357687 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[Br:12]Br>[Fe]>[Br:12][C:7]1[CH:6]=[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:4]=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6269P-ToluenesulfonamideHCID 24408Bromine

Product 1

HCID 184001173-Bromo-4-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a mixture of p-toluenesulfonamide (2 g, 1.16 mmol) and iron (0.41 g, 7.36 mmol) was slowly added bromine (6 mL, 116 mmol). The resulting reddish brown solution was stirred at RT for 1 h. The reaction was carefully poured into ice-cold 1 M Na2S2O3 aqueous solution and extracted with CH2Cl2 (2×). The organic extracts were combined and washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. CombiFlash purification (1% to 10% MeOH/CH2Cl2) afforded the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): □ 7.98 (s, 1H), 7.71 (d, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.54 (br s, 2H), 2.41 (s, 3H).

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customCombiFlash purification (1% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-41595d5235204eeaa1b6ada8e32aab83
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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