Azobisisobutyronitrile → Methyl 2-(4-bromomethylphenoxy)-2-(2-chlorophenyl)acetate

HRID 5925Notes

Reaction equation

HRID 5925 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:8]([O:10][CH3:11])=[O:9])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385716Methyl 2-(2-chlorophenyl)-2-(4-methylphenoxy)acetate

Product 1

HCID 19385740Methyl 2-(4-bromomethylphenoxy)-2-(2-chlorophenyl)acetateYield 73%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the product of Example 3, Step B (0.2 g, 0.69 mmol), N-bromosuccinimide (117 mg, 166 mmol) and a catalytic amount of AIBN in 2 ml CCl4 was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo and chromatographed on silica gel (125×20 mm) eluting with 5% ethyl acetate in hexane. The product was isolated in a 73% yield (186 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customchromatographed on silica gel (125×20 mm)
  3. washeluting with 5% ethyl acetate in hexane
  4. customThe product was isolated in a 73% yield (186 mg)

Sources & evidence

ORD record
ord-52fd80fbaf8b482ba702acb847f8a77a
Source dataset
uspto-grants-1993_09
Patent number
US05246944

Reaction notes

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