Benzoyl Peroxide → 3-Bromomethyl-2-[(4-methoxybenzenesulfonyl)-methylamino]-benzoic acid methyl ester

HRID 583349Notes

Reaction equation

HRID 583349 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:12].[Br:25]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:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][Br:25])[C:5]=1[N:11]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)(=[O:15])=[O:14])[CH3:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 700522562-[(4-Methoxybenzenesulfonyl)-methylamino]-3-methyl-benzoic acid methyl ester

Product 1

HCID 700532293-Bromomethyl-2-[(4-methoxybenzenesulfonyl)-methylamino]-benzoic acid methyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.723 g (2.072 mmol) of the product of Example 187 in 70 mL of carbon tetrachloride was added 0.406 g (2.279 mmol) of N-bromosuccinimide and 0.14 g of dibenzoyl peroxide. The resulting mixture was heated to reflux for 18 h and then cooled to room temperature, washed with sodium bisulfite solution and water, dried over MgSO4, filtered and concentrated in vacuo. The residue was titurad with ether/hexanes (1:1) and then filtered to provide 0.504 g (57%) of the desired product as a white solid. Electrspray Mass Spec: 428 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 18 h
  3. washwashed with sodium bisulfite solution and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d79f9ce530dc49908d7276edc2f50ec7
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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