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

HRID 405155Notes

Reaction equation

HRID 405155 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-a74ba8239c05478da1e191458d0674b0
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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