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

HRID 1500402Notes

Reaction equation

HRID 1500402 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.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>ClC(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:13])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27756354-Methyl-3-(trifluoromethyl)bromobenzene

Product 1

HCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzeneYield 53.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In the case of compound 11, the required intermediate for step a) was synthesised as follows: To a stirred solution of 4-bromo-1-methyl-2-trifluoromethylbenzene (10 g) in tetrachloromethane (100 ml) at room temperature is added N-bromosuccinimide (7.5 g) and azobisisobutyronitrile (700 mg). After 15 h of stirring at reflux, the reaction is allowed to cool to room temperature, water is added and the reaction mixture is extracted twice with ethyl acetate. The organic layer is washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (9:1 cyclohexane:ethyl acetate) to yield 4-bromo-1-bromomethyl-2-trifluoromethylbenzene (7.1 g).

Workup

  1. temperatureat reflux
  2. extractionthe reaction mixture is extracted twice with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (9:1 cyclohexane:ethyl acetate)

Sources & evidence

ORD record
ord-248f0ad2ce9e4d9988a041a7041e9123
Source dataset
uspto-grants-2015_12
Patent number
US09206164B2

Reaction notes

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