Carbon Tetrachloride → 4-(Bromomethyl)-3-chlorobenzene-1-sulfonyl chloride

HRID 327796Notes

Reaction equation

HRID 327796 reaction equation
[Br:1]N1C(=O)CCC1=O.Cl[C:10]1[CH:11]=[C:12](C)[CH:13]=[CH:14][C:15]=1[S:16]([Cl:19])(=[O:18])=[O:17].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:39]([Cl:43])(Cl)(Cl)Cl>>[Cl:43][C:39]1[CH:10]=[C:15]([S:16]([Cl:19])(=[O:18])=[O:17])[CH:14]=[CH:13][C:12]=1[CH2:11][Br:1]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2890812-chloro-4-methylbenzenesulfonyl chloride

Product 1

HCID 193849654-(Bromomethyl)-3-chlorobenzene-1-sulfonyl chlorideYield 14%

Procedure

N-Bromosuccinimide (13.76 g, 76 mmol) was added to a stirred solution of 3-chloro-4-toluenesulphonyl chloride (12 g, 76 mmol) in CCl4 (120 ml) under argon. After one hour benzoyl peroxide (0.92 g, 3.8 mmol) was added and the reaction mixture refluxed overnight. The mixture was allowed to cool, the resulting white precipitate filtered off and the filtrate evaporated to a yellow oil. Purification of the residue by chromatography over silica gel (3% ethyl acetate in hexane) afforded 3-chloro-4-bromomethylphenylsulphonyl chloride (3.3 g, 14%) as a colourless oil.

Workup

  1. temperaturethe reaction mixture refluxed overnight
  2. temperatureto cool
  3. filtrationthe resulting white precipitate filtered off
  4. customthe filtrate evaporated to a yellow oil
  5. customPurification of the residue by chromatography over silica gel (3% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-27b53852cfc74f79abbf2bfebce31d4f
Source dataset
uspto-grants-1993_12
Patent number
US05274094

Reaction notes

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