Benzoyl Peroxide → 2-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene

HRID 846028Notes

Reaction equation

HRID 846028 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:12].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH2:12][Br:15]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene

Product 1

HCID 106781242-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzeneYield 88.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A 500 mL round bottomed flask was charged with 250 mL of carbon tetrachloride 15.90 g. of 2-(trifluoromethyl)-6-nitrotoluene, 27.60 g. of N-bromosuccinimide, and 11.8 g of benzoyl peroxide. This mixture was brought under reflux and stirred at this temperature for 14 h. The mixture was cooled, filtered and 9.94 g of N-bromosuccinimide together with 4.2 g of benzoyl peroxide was added to the filtrate. This mixture was brought under reflux for 14 h. The mixture was cooled, filtered and the filtrate was stripped of solvent. The crude product was chromatographed on a SiO2 column to give 19.57 g (88.9% yield) of pure product.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. addition9.94 g of N-bromosuccinimide together with 4.2 g of benzoyl peroxide was added to the filtrate
  5. temperatureunder reflux for 14 h
  6. temperatureThe mixture was cooled
  7. filtrationfiltered
  8. customThe crude product was chromatographed on a SiO2 column

Sources & evidence

ORD record
ord-c77c48c2d6b54fac95e5a0044310efba
Source dataset
uspto-grants-1992_08
Patent number
US05135838

Reaction notes

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