Azobisisobutyronitrile → 1-(5-Bromomethylpyridin-2-yl)cyclopentanecarboxlic acid ethyl ester

HRID 481402Notes

Reaction equation

HRID 481402 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C1C(=O)N([Br:25])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][Br:25])=[CH:13][N:12]=2)[CH2:7][CH2:8][CH2:9][CH2:10]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 572450121-(5-Methylpyridin-2-yl)cyclopentane carboxylic acid ethyl ester2×

Product 1

HCID 701035861-(5-Bromomethylpyridin-2-yl)cyclopentanecarboxlic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture containing the product of Step 2, above (44) (1 equiv.), n-bromosuccinimide (1.1 equiv.), CCl4 and a catalytic amount of azobisisobutyronitrile was heated at reflux for 4 hours, cooled to 0° C. and filtered through celite. The residue was washed well with CCl4 and the filtrate was concentrated and chromatographed on silica gel to yield the title compound (45).

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationfiltered through celite
  3. washThe residue was washed well with CCl4
  4. concentrationthe filtrate was concentrated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-7289d1e66d054edab6bb6e540f7037b8
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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