N-bromobutanimide → Methyl 6-bromohexa-2,4-dienoate

HRID 2245755

Reaction equation

HRID 2245755 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].[Br:10]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[CH3:9][O:8][C:1](=[O:7])[CH:2]=[CH:3][CH:4]=[CH:5][CH2:6][Br:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5323650Methyl sorbate

Product 1

HCID 54529347Methyl 6-bromohexa-2,4-dienoateYield 65%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of methyl sorbate (1.26 g, 10 mmol) and N-bromosuccinimide (1.98 g, 11.0 mmol) in chlorobenzene was irradiated with a 250 W sunlamp so as to achieve a state of reflux for 4 hours. The (cooled) mixture was then evaporated under reduced pressure to give a brown oil which was purified by column chromatography (9:1 60-80° C. petroleum ether:diethyl ether) to give the title compound (1.33 g, 65%) as a clear oil.

Workup

  1. customwas irradiated with a 250 W sunlamp so as
  2. temperatureof reflux for 4 hours
  3. temperatureThe (cooled) mixture
  4. customwas then evaporated under reduced pressure
  5. customto give a brown oil which
  6. customwas purified by column chromatography (9:1 60-80° C. petroleum ether:diethyl ether)

Sources & evidence

ORD record
ord-1146c5a374d842eaabd15815d813bf26
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Linked notes

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