Benzoyl Peroxide → Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate

HRID 2228012Notes

Reaction equation

HRID 2228012 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:3]=1.[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

Product 1

HCID 18474595Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoateYield 55%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 4-methyl-2-trifluoromethylsulfonyloxybenzoate (23.79 g; 7.9 mmol), N-bromosuccinimide (14.19 g; 7.9 mmol), 2,2-azobis (2′-methylproprionitrile) (0.5 g; 3 mmol) and benzoylperoxide (0.5 g; 2 mmol) in tetrachloromethane (250 ml) was heated at reflux for 6 hours. The solid was filtered and the filtrate evaporated to dryness to give methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate. Yield=55%.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationThe solid was filtered
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-3ff81642c67640e6971a898d91403f0f
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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