N-bromobutanimide → HCID 13176302, compound

HRID 1981304Notes

Reaction equation

HRID 1981304 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:24]=[CH:23][C:13]([O:14][CH2:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH:18]=[CH2:19])=[CH:12][CH:11]=1>ClC(Cl)(Cl)Cl>[Br:1][CH:15]([O:14][C:13]1[CH:23]=[CH:24][C:10]([Cl:9])=[CH:11][CH:12]=1)[C:16](=[O:22])[C:17]([CH3:20])([CH3:21])[CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 13176301HCID 13176301, compound

Product 1

HCID 13176302HCID 13176302, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
5 °C

Procedure

12.5 g (0.07 mol) of N-bromosuccinimide were added to a solution of 16.7 g (0.07 mol) of 5-(4-chlorophenoxy)-3,3-dimethylpent-1-en-4-one and a pinch of azoisobutyronitrile in 200 ml of tetrachloromethane. The mixture was then heated at the boil for 8 hours, under UV irradiation. The mixture was then cooled to 5° C. and filtered off from the precipitated succinimide. The filtrate was concentrated in vacuo. 23 g of crude 5-bromo-5-(4-chlorophenoxy)-3,3-dimethylpent-1-en-4-one were obtained as an oil, which was directly reacted further. ##STR29##

Workup

  1. temperatureThe mixture was then heated at the boil for 8 hours, under UV irradiation
  2. filtrationfiltered off from the precipitated succinimide
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4feddf0a4d574966ac07cfd7fb7c288e
Source dataset
uspto-grants-1985_04
Patent number
US04514409

Reaction notes

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