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

HRID 2399924Notes

Reaction equation

HRID 2399924 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, 3.8i 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% ethyi 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% ethyi acetate in hexane)

Sources & evidence

ORD record
ord-09312d978a814ace873a93a413821fc3
Source dataset
uspto-grants-1995_09
Patent number
US05451676

Reaction notes

Loading…