N-bromobutanimide → 4-(Bromomethyl)-3-trifluoromethylbenzenesulphonyl chloride

HRID 1108998Notes

Reaction equation

HRID 1108998 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([S:10]([Cl:13])(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([S:10]([Cl:13])(=[O:12])=[O:11])=[CH:4][C:3]=1[C:2]([F:1])([F:14])[F:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 189565564-Methyl-3-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 189565524-(Bromomethyl)-3-trifluoromethylbenzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

64.6 g (0.25 mol) of 3-trifluoromethyl-4-methylbenzenesulphonyl chloride are taken up in 500 ml of carbon tetrachloride and, after addition of 44.5 g (0.25 mol) of N-bromosuccinimide and 0.4 g of ABN, the mixture is heated under reflux for 24 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 33.9 g (40% of theory) of the title compound. Rf : 0.41 (petroleum ether/toluene 3:1).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. filtrationthe solids are filtered off

Sources & evidence

ORD record
ord-604aa369d2a04746883ca191a567bc8a
Source dataset
uspto-grants-1994_06
Patent number
US05318980

Reaction notes

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