Azobisisobutyronitrile → tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

HRID 37218Notes

Reaction equation

HRID 37218 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.N(C(C)(C)C#N)=NC(C)(C)C#N.C1C(=O)N([Br:40])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:40][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 15234721Tert-butyl 2-cyclopentyl-2-(4-methylphenyl)acetate

Product 1

HCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

27.4 g (0.1 mol) of tert-butyl 2-cyclopentyl-2-(4-methylphenyl)-acetate are dissolved in 200 ml of carbon tetrachloride and the solution is heated to boiling point. After an addition of 0.82 g of azobisisobutyronitrile, 18.7 g (0.105 mol) of n-bromosuccinimide are added in portions, the mixture is subsequently refluxed for 1 hour and cooled to 0° C., and succinimide is filtered off. After concentration of the filtrate, the product precipitates. It is washed with petroleum ether (40/60) and dried. Yield: 20 g (57% of theory)

Workup

  1. temperaturethe solution is heated
  2. additionare added in portions
  3. temperaturethe mixture is subsequently refluxed for 1 hour
  4. filtrationsuccinimide is filtered off
  5. customAfter concentration of the filtrate, the product precipitates
  6. washIt is washed with petroleum ether (40/60)
  7. customdried

Sources & evidence

ORD record
ord-511f0f3d81054092a7468778ef1b0c79
Source dataset
uspto-grants-1995_05
Patent number
US05420149

Reaction notes

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