Benzoyl Peroxide → 4-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

HRID 2194866Notes

Reaction equation

HRID 2194866 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:20])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27756354-Methyl-3-(trifluoromethyl)bromobenzene

Product 1

HCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of commercially available 4-bromo-1-methyl-2-(trifluoromethyl)benzene (1 eq.), NBS (1.1 eq.) and a catalytic amount of benzoyl peroxide in CCl4 (0.21M) was stirred at room temperature for 1 h under a 150 W spot lamp. The mixture was concentrated, purification by column chromatography on silica gel, eluting with Hex, afforded the desired material as an oil.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurification by column chromatography on silica gel
  3. washeluting with Hex

Sources & evidence

ORD record
ord-1187550e37de4583ae3fcfc85b975dea
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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