Carbon Tetrachloride → 4-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

HRID 66977

Reaction equation

HRID 66977 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)([OH:3])=[O:2].[Br:16]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>CO>[Br:16][CH:13]1[CH2:12][C:11](=[O:15])[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:14]1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 789025-Oxo-1-cyclopentene-1-heptanoic acid

Product 1

HCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

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).

Workup

  1. additionA stirred mixture of 35.9 g
  2. filtrationfiltered
  3. washThe filtrate is washed with cold water
  4. dry with materialdried over magnesium sulfate
  5. customto give an oil, λmax

Sources & evidence

ORD record
ord-425c92aa933c403aa6c1aaedb226d17f
Source dataset
uspto-grants-1982_08
Patent number
US04343949

Linked notes

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