Water → 4-(bromomethyl)-3-(trifluoromethyl)benzonitrile

HRID 1922016Notes

Reaction equation

HRID 1922016 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27755984-Methyl-3-(trifluoromethyl)benzonitrile

Product 1

HCID 588271604-(bromomethyl)-3-(trifluoromethyl)benzonitrileYield 98.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-methyl-3-(trifluoromethyl)benzonitrile (10 g, 54 mmol) was dissolved in 200 mL of carbon tetrachloride and treated with N-bromosuccinimide (10.5 g, 59 mmol) and benzoyl peroxide (1.3 g, 0.54 mmol). The reaction mixture was heated to reflux temperature and stirred for one week. Then, 80 mL of water was added and the layers were separated. The aqueous layer was extracted with methylene chloride (2×50 mL). The combined organic layers were washed with water (2×50 mL), dried over magnesium sulfate, and concentrated to provide 4-(bromomethyl)-3-(trifluoromethyl)benzonitrile (14 g, 53 mmol) as a yellow oil which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with methylene chloride (2×50 mL)
  5. washThe combined organic layers were washed with water (2×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec72eb13e95c470ba210fd4edaf5b626
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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