Benzoyl Peroxide → HCID 59610037, compound

HRID 524382Notes

Reaction equation

HRID 524382 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([Cl:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[CH:4]([Br:16])[C:5]1[CH:6]=[CH:7][C:8]([S:11]([Cl:14])(=[O:13])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 23388822methyl 2-(4-(chlorosulfonyl)phenyl)acetate

Product 1

HCID 59610037HCID 59610037, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(4-Chlorosulfonyl-phenyl)-acetic acid methyl ester (13 g, 52.41 mmol) was taken in carbon tetrachloride (262 mL). N-Bromosuccinimide (10.26 g, 57.66 mmol) was added in one lot followed by benzoyl peroxide (1.39 g, 5.766 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. Product was purified using column chromatography in 3% ethyl acetate:hexane which yielded bromo-(4-chlorosulfonyl-phenyl)-acetic acid methyl ester (2.8 g) as a gummy mass.

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
  6. customProduct was purified

Sources & evidence

ORD record
ord-1bcac4e2959b452fb8f92539da831508
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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