N-bromobutanimide → Ethyl 6-bromo-2,3,3-trimethylhex-4-enoate

HRID 359177Notes

Reaction equation

HRID 359177 reaction equation
[CH3:1][CH:2]([C:8]([CH3:13])([CH3:12])[CH:9]=[CH:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:14]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:11][CH:10]=[CH:9][C:8]([CH3:13])([CH3:12])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 54109182Ethyl 2,3,3-trimethylhex-4-enoate

Product 1

HCID 54437039Ethyl 6-bromo-2,3,3-trimethylhex-4-enoateYield 86.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 920 mg (5 mmoles) of ethyl 2,3,3-trimethyl-4-hexenoate, 10 ml of carbon tetrachloride, 107 mg (6 mmoles) of N-bromosuccinimide, and 50 mg of benzoyl peroxide was heated under reflux for about two hours. The insoluble succinimide was removed by filtration. The filtrate was washed successively with saturated aqueous sodium bicarbonate solution and water, then dried over magnesium sulfate. The dried solution was distilled to give 1.14 g (86% yield) of ethyl 6-bromo-2,3,3-trimethyl-4-hexenoate, b.p. 80°-81°/0.8 mm.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for about two hours
  3. customThe insoluble succinimide was removed by filtration
  4. washThe filtrate was washed successively with saturated aqueous sodium bicarbonate solution and water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe dried solution was distilled

Sources & evidence

ORD record
ord-82c199ab5d66468083d5a860c702bded
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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