N-bromobutanimide → 3-(Bromomethyl)-4-chlorobenzonitrile

HRID 1260902Notes

Reaction equation

HRID 1260902 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>C(CC(O)=O)(C)(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:11][CH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[Cl:1])[C:6]#[N:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 38655354-Chloro-3-methylbenzonitrile

Product 1

HCID 666777673-(Bromomethyl)-4-chlorobenzonitrileYield 98.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 14057tert-Butylacetic acidSolvent

Conditions

Temperature
90 °C

Procedure

(Step 1) To a solution of 4-chloro-3-methylbenzonitrile (1 g) in t-butylacetic acid (10 ml) were added N-bromosuccinimide (1.5 g) and azobisisobutyronitrile (0.05 g), and the mixture was stirred at 90° C. for 12 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:1-1:9) to give 3-(bromomethyl)-4-chlorobenzonitrile (1.5 g) as a white solid.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:1-1:9)

Sources & evidence

ORD record
ord-15630ec8c13d47c1a040af2118746abc
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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