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

HRID 1594653Notes

Reaction equation

HRID 1594653 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 986221-(4-Methylphenyl)cyclopentanecarboxylic acid

Product 1

HCID 217065091-(4-Bromomethylphenyl)cyclopentane carboxylic acidYield 133.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-(4-methylphenyl)cyclopentane carboxylic acid tbutyl 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 tbutyl 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-c86c967879c94697bce1fd1ac7641177
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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