N-bromobutanimide → HCID 18759659, compound

HRID 432564Notes

Reaction equation

HRID 432564 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7].[Br:16]N1C(=O)CCC1=O>N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.FC1C=CC=CC=1>[Br:16][CH2:15][C:12]1[CH:13]=[CH:14][C:2]([Cl:1])=[C:3]([CH:11]=1)[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 4508432HCID 4508432, compound

Product 1

HCID 18759659HCID 18759659, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)CatalystHCID 10008FluorobenzeneSolvent

Procedure

Into 150 ml of fluorobenzene was dissolved 5.61 g of methyl 2-(2-chloro-5-methylphenoxy)propionate obtained above; 4.37 g of N-bromosuccinimide and then 0.2 g of 1,1′-azobis(cyclohexanecarbonitrile) were added, and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the solution was allowed to left for cooling; the reaction solution was filtered; the filtrate was concentrated under reduced pressure; and the residue was subjected to silica gel chromatography to give 6.59 g of methyl 2-[5-(bromomethyl)-2-chlorophenoxy]propionate.

Workup

  1. customobtained above
  2. temperatureunder reflux for 2 hours
  3. waitto left
  4. temperaturefor cooling
  5. filtrationthe reaction solution was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38d000ce502c476d86f65fa72986b84e
Source dataset
uspto-grants-2003_12
Patent number
US06664214B1

Reaction notes

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