Benzoyl Peroxide → 4-(Bromomethyl)-3-fluorobenzenesulphonyl chloride

HRID 1108997Notes

Reaction equation

HRID 1108997 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([Cl:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27786003-Fluoro-4-methylbenzene-1-sulfonyl chloride

Product 1

HCID 189565534-(Bromomethyl)-3-fluorobenzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

20.9 g (0.1 mol) of 3-fluoro-4-methylbenzenesulphonyl chloride are taken up in 200 ml of carbon tetrachloride and, after addition of 19.6 g (0.11 mol) of N-bromosuccinimide and 0.3 g of dibenzoyl peroxide, the mixture is heated under reflux for 5 hours. After cooling, the solids are filtered off and the filtrate is freed from the solvent. Flash chromatography with petroleum ether/toluene (4:1), 50 μm particle size, gives 12.4 g (44% of theory) of the title compound. Rf : 0.42 (petroleum ether/toluene 3:1).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe solids are filtered off

Sources & evidence

ORD record
ord-d8ef883451844540b4157f30177ce43e
Source dataset
uspto-grants-1994_06
Patent number
US05318980

Reaction notes

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