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

HRID 1387263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387263
[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(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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 217065091-(4-Bromomethylphenyl)cyclopentane carboxylic acidAusbeute 133,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7187Benzoyl PeroxideKatalysator

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5ba42a46e2894196bf473c19833601c4
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268365B1

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