Benzoyl Peroxide → Bromo-(4-chlorosulfonyl-phenyl)-acetic acid ethyl ester

HRID 1889169Notes

Reaction equation

HRID 1889169 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([Br:17])[C:6]1[CH:7]=[CH:8][C:9]([S:12]([Cl:15])(=[O:13])=[O:14])=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10467900(4-Chlorosulfonyl-phenyl)-acetic acid ethyl ester

Product 1

HCID 59610030Bromo-(4-chlorosulfonyl-phenyl)-acetic acid ethyl esterYield 94.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(4-Chlorosulfonyl-phenyl)-acetic acid ethyl ester (1.6 gm, 6.45 mmol) was taken in carbon tetrachloride (13 ml). N-Bromosuccinimide (1.26 gm, 7.09 mmol) was added in one lot followed by benzoyl peroxide (171 mg, 0.7 mmol). The reaction mixture was refluxed for 2 days. The reaction mixture was cooled to room temperature and filtered; filtrate was washed with water followed by brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide bromo-(4-chlorosulfonyl-phenyl)-acetic acid ethyl ester (2.08 gm) as a gummy mass. The crude material was used as such for further reaction.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. filtrationfiltered
  3. washfiltrate was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bbfbe1f19fe142cb8955f006d7e9de3d
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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