N-bromobutanimide → Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate

HRID 2121178Notes

Reaction equation

HRID 2121178 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:20])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:17])([F:16])[F:18])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

Product 1

HCID 18474595Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoateYield 80.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-(trifluoromethanesulfonyloxy)-4-methylbenzoic acid methyl ester (19.6 g, 65.8 mmol), prepared as in Example 204A, in 250 mL CCl4 was added N-bromosuccinimide (12.29 g, 69.1 mmol) followed by 2,2′-azobisisobutyronitrile (108 mg, 0.658 mmol) and the reaction was heated to reflux. After 16 hours, the reaction was evaporated and the residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes) to give 19.9 g (80%) of 2-(trifluoromethanesulfonyloxy)-4-bromomethylbenzoic acid methyl ester as a yellow oil.

Workup

  1. temperaturethe reaction was heated to reflux
  2. customthe reaction was evaporated
  3. customthe residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-021253110724429d8d88c46e39a6e0e1
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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