Azobisisobutyronitrile → 3-(4-Chlorophenyl)-3-bromopropyl methyl ether

HRID 1634373Notes

Reaction equation

HRID 1634373 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)CCl>[CH3:1][O:2][CH2:3][CH2:4][CH:5]([C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1)[Br:13]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 120566453-(4-Chlorophenyl)propyl methyl ether

Product 1

HCID 120566463-(4-Chlorophenyl)-3-bromopropyl methyl etherYield 108.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-(4-chlorophenyl)propyl methyl ether (8.6 g, 46.5 mmol), N-bromosuccinimide (NBS; 9.43 g, 52.9 mmol), and a catalyst amount of 2,2′-azobisisobutyronitrile in ethylene dichloride (236 ml) was heated at 65° to 70° C. for three hours. The cooled reaction mixture was washed successively with water, saturated aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford crude title compound (13.3 g) which was used without further purification.

Workup

  1. customThe cooled reaction mixture
  2. washwas washed successively with water, saturated aqueous sodium bicarbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab1b445fb6f74e288a677a46d9927c0c
Source dataset
uspto-grants-2003_01
Patent number
US06506800B2

Reaction notes

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