Azobisisobutyronitrile → Ethyl 2-(4-bromomethylphenoxy)phenylacetate

HRID 1492302Notes

Reaction equation

HRID 1492302 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:24][CH:23]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18952394Ethyl 2-(4-methylphenoxy)phenylacetate

Product 1

HCID 18952399Ethyl 2-(4-bromomethylphenoxy)phenylacetateYield 45.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (6.64 g) and azo(bisisobutyronitrile) (400 mg) were added to a solution of compound (B) (10.1 g) in carbon tetrachloride (100 ml). The mixture was heated under reflux for 20 hours and then cooled to ambient temperature. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:19 v/v), to give ethyl 2-(4-bromomethylphenoxy)phenylacetate (C) (5.9 g), as an oil; NMR (d6 -DMSO): 1.15(t, 3H), 4.1(q, 2H), 4.65(s, 2H), 6.0(s, 1H), 6.95(d, 2H), 7.3-7.5(m, 5H), 7.5-7.6(m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:19 v/v)

Sources & evidence

ORD record
ord-f02613f6a2514657b7084442881159c7
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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