Azobisisobutyronitrile → Methyl 2-(4-bromomethylphenoxy)phenylacetate

HRID 37223Notes

Reaction equation

HRID 37223 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 13729875Methyl 2-(4-methylphenoxy)phenylacetate

Product 1

HCID 19934852Methyl 2-(4-bromomethylphenoxy)phenylacetateYield 51.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the product of Step B (50 mg, 0.205 mmol) NBS (33 mg, 0.9 eq) and AIBN (5 mg, catalytic amount) in CCl4 (2 mL) was heated to reflux for 2 hours, and then concentrated in vacuo. The residue was chromatographed on a flash silica column (20×140 mm) eluted with 5% ethyl acetate/hexane to yield 32 mg (48%) of product (Rf =0.17, 5% ethyl acetate/hexane).

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on a flash silica column (20×140 mm)
  4. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-5bb3ad0af20f415ba10f1535c32047fd
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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