Azobisisobutyronitrile → 4-Bromo-2-bromomethyl-benzoic acid isopropyl ester

HRID 1869959Notes

Reaction equation

HRID 1869959 reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH3:13])([CH3:3])[CH3:2].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][Br:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 225688974-Bromo-2-methyl-benzoic acid isopropyl ester2×

Product 1

HCID 574242524-Bromo-2-bromomethyl-benzoic acid isopropyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-bromo-2-methyl-benzoic acid isopropyl ester (Intermediate 117, 6.12 g, 23.8 mmol) in carbon tetrachloride (120 mL) was treated with N-bromosuccinimide (4.6 g, 26.18 mmol) and 2,2′-azobisisobutyronitrile (0.6 g) and the resulting reaction mixture was refluxed overnight. It was cooled to ambient temperature, the solids were filtered off and washed with 1:1 hexane:diethyl ether, and the filtrate and washings were evaporated in vacuo to afford an oil (5.1 g, 64%) that was used as such for the next step.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. filtrationthe solids were filtered off
  4. washwashed with 1:1 hexane
  5. customdiethyl ether, and the filtrate and washings were evaporated in vacuo

Sources & evidence

ORD record
ord-38a9bf36df484be18bcaa797bdf5fe65
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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