Azobisisobutyronitrile → 4-(Bromomethyl)benzenesulfonyl chloride

HRID 1108996Notes

Reaction equation

HRID 1108996 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 73974-Toluenesulfonyl chlorideHCID 67184N-bromobutanimide

Product 1

HCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

38.1 g (0.2 mol) of 4-methylbenzenesulphonyl chloride are dissolved in 300 ml of carbon tetrachloride, 35.6 g (0.2 mol) of N-bromosuccinimide are added and, after addition of 0.2 g (1.2 mmol) of azobisisobutyronitrile (ABU), the mixture is heated under reflux for 4 hours. After cooling, the solids are filtered off and the filtrate is freed from the solvent. Flash chromatography (petroleum ether/toluene 4:1, 50 μm particle size) and subsequent recrystallisation from 100 ml of cyclohexane gives 24.0 g (45% of theory) of the title compound. Rf =0.75 (toluene)

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. filtrationthe solids are filtered off
  5. customFlash chromatography (petroleum ether/toluene 4:1, 50 μm particle size) and subsequent recrystallisation from 100 ml of cyclohexane

Sources & evidence

ORD record
ord-d1a8c92d3d3a46fa97a0956d1a1d78a6
Source dataset
uspto-grants-1994_06
Patent number
US05318980

Reaction notes

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