N-bromobutanimide → 3-(Bromomethyl)phenyl acetate

HRID 1351087Notes

Reaction equation

HRID 1351087 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Br:12]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][Br:12])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67406Cresatin

Product 1

HCID 64220753-(Bromomethyl)phenyl acetateYield 100.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of m-tolyl acetate (583 mg), N-bromosuccinimide (691 mg) and α,α′-azobis(isobutyronitrile) (13 mg) in tetrachloromethane (10 mL) was refluxed for 1 hour. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. The filtrate was concentrated to give the title compound (893 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customthe insoluble material was removed by filtration
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d803bf4dc0984eeba3872c4297924e16
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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