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

HRID 1197656Notes

Reaction equation

HRID 1197656 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 ol.

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-9bebd459c6004f568249fdc1c8a5e7f2
Source dataset
uspto-grants-1994_01
Patent number
US05276153

Reaction notes

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