Reaktion #95255

Reaktionsgleichung

2-(6-carboxyhexyl) cyclopent-2-en-1-one

N-bromosuccinimide

carbon tetrachloride

→

4-bromo-2(6-carboxyhexyl)cyclopent-2-en-1-one

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA stirred mixture of 35.9 g
2. 2
   Filtrationfiltered
3. 3
   WaschenThe filtrate is washed with cold water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Sonstigeto give an oil, λmax

Vorschrift

A stirred mixture of 35.9 g. (0.171 moles) of 2-(6-carboxyhexyl) cyclopent-2-en-1-one [Bagli et al., Tetrahedron Letters, No. 5, 465 (1966)], 35.0 g. (0.197 moles) of N-bromosuccinimide, and 600 ml. of carbon tetrachloride is refluxed for 35 minutes. The mixture is cooled to 5° C. and filtered. The filtrate is washed with cold water, dried over magnesium sulfate, and taken to dryness to give an oil, λmax.MeOH =225 mμ (8850); νmax.=1705 (carbonyl groups) and 1625. cm-1 (olefin group).

Quelle