N-bromobutanimide → 1-(4-Bromomethylphenyl)cyclopentane carboxylic acid t butyl ester

HRID 1274264Notes

Reaction equation

HRID 1274264 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][Br:20])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 206745431-(4-Methylphenyl)cyclopentane carboxylic acid t butyl ester

Product 1

HCID 206745421-(4-Bromomethylphenyl)cyclopentane carboxylic acid t butyl esterYield 111.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-(4-methylphenyl)cyclopentane carboxylic acid t butyl ester (2.00 g, 7.68 mmol) in CCl4 (80 mL) was added N-bromosuccinimide (1.37 g, 7.68 mmol) and benzoyl peroxide (0.050 g). This mixture was brought to reflux by heating, and maintained at reflux for 2 hours using a sun lamp (250 W). Additional N-bromosuccinimide (0.34 g, 1.9 mmol) was added, and after 20 minutes the solution was concentrated to 40 mL. The white precipitate was removed by filtration. The filtrate was concentrated to give 1-(4-bromomethylphenyl)cyclopentane carboxylic acid t butyl ester (2.9 g, 100%) as a yellow oil which was used without additional purification.

Workup

  1. temperatureto reflux
  2. temperatureby heating
  3. temperaturemaintained
  4. temperatureat reflux for 2 hours
  5. concentrationafter 20 minutes the solution was concentrated to 40 mL
  6. customThe white precipitate was removed by filtration
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a59d1e4fcef5441e9d4def335ff86ee2
Source dataset
uspto-grants-2000_12
Patent number
US06156784

Reaction notes

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