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

HRID 1707264Notes

Reaction equation

HRID 1707264 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.[Br:33]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:33][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-methyl-phenyl)-acetate are dissolved in 200 ml of carbon tetrachloride and the solution is heated to boiling. After addition of 0.82 g of azobisisobutyronitrile, 18.7 g (0.105 mol) of N-bromosuccinimide are added in portions and the mixture is then refluxed for 1 h, cooled to 0° C. and filtered off from the succinimide. After concentration of the filtrate the product precipitates. It is washed with petroleum ether (40:60) and dried. Yield: 20 g (57% of theory) Solidification point 73°-76° C.

Workup

  1. temperaturethe solution is heated to boiling
  2. additionare added in portions
  3. temperaturethe mixture is then refluxed for 1 h
  4. filtrationfiltered off from the succinimide
  5. customAfter concentration of the filtrate the product precipitates
  6. washIt is washed with petroleum ether (40:60)
  7. customdried
  8. customYield: 20 g (57% of theory) Solidification point 73°-76° C.

Sources & evidence

ORD record
ord-70c3e313328f487eb92af36dc0515f3c
Source dataset
uspto-grants-1994_10
Patent number
US05352687

Reaction notes

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