Hydrogen Peroxide → 3-(3-Bromopropyl)benzamide

HRID 1608726Notes

Reaction equation

HRID 1608726 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]#[N:12])[CH:8]=[CH:9][CH:10]=1.C(=O)(O)[O-:14].[K+].OO.O>CO.C(=O)([O-])[O-].[K+].[K+]>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:11]([NH2:12])=[O:14]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 516893Potassium BicarbonateHCID 193772303-(3-Bromopropyl)benzonitrile

Product 1

HCID 193772323-(3-Bromopropyl)benzamideYield 298.9%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 887MethanolSolvent

Procedure

To 15.2 g (0.067 mole) of 3-(3-bromopropyl)cyanobenzene (the product of step (c)) in 55 ml methanol, 2.2 g potassium bicarbonate was added; to that mixture, 15.2 ml of 30% hydrogen peroxide was added dropwise. The reaction mixture was stirred for about 45 minutes. Then, 113 mg potassium carbonate was added and the resulting mixture was stirred overnight. Water (about 35 ml) was added to the reaction mixture and the resulting solution put in a freezer for about 50 minutes. The solid was collected by filtration and dried overnight to give 15.9 g of the above-identified product as a solid, melting point 109° C.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. waitthe resulting solution put in a freezer for about 50 minutes
  3. filtrationThe solid was collected by filtration
  4. customdried overnight

Sources & evidence

ORD record
ord-b7960b64df6d497d8639d93e06203aa5
Source dataset
uspto-grants-1995_03
Patent number
US05395970

Reaction notes

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