Benzene → 2-Bromo-1-(bromomethyl)-4-(trifluoromethyl)benzene

HRID 2167126Notes

Reaction equation

HRID 2167126 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C=CC=CC=1.[Br:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[CH3:36].C1C(=O)N([Br:44])C(=O)C1>CCOC(C)=O>[Br:25][C:26]1[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][C:27]=1[CH2:36][Br:44]

Participants

6

Reactant 4

HCID 241BenzeneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27793762-Bromo-1-methyl-4-(trifluoromethyl)benzene

Product 1

HCID 149499362-Bromo-1-(bromomethyl)-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Solid benzoyl peroxide (1.5 g, 6.3 mmol) was added to a benzene solution (200 mL) of 2-bromo-1-methyl-4-(trifluoromethyl)benzene (10.0 g, 41.8 mmol) and NBS (8.2 g, 46.0 mmol) and the resulting mixture was refluxed. After 16 h the resulting mixture was cooled, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperatureAfter 16 h the resulting mixture was cooled
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customdry

Sources & evidence

ORD record
ord-0d199021d8924a9c972e133f47df041a
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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