N-bromobutanimide → 1-(Bromomethyl)-2-chloro-4-methoxybenzene

HRID 993226Notes

Reaction equation

HRID 993226 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][Br:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 69517572-Chloro-4-methoxytoluene

Product 1

HCID 223274281-(Bromomethyl)-2-chloro-4-methoxybenzeneYield 90.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

186 g of 2-chloro-4-methoxytoluene are dissolved in 1000 ml of carbon tetrachloride and, together with 212 g of N-bromosuccinimide, heated at reflux for 2 h while 2.4 g of AIBN are added. The solid is filtered off and washed with a small amount of carbon tetrachloride, the filtrate is concentrated, and the residue which remains is fractionated. 252 g of orange oil are obtained (Purity 82%).

Workup

  1. temperatureheated
  2. additionare added
  3. filtrationThe solid is filtered off
  4. washwashed with a small amount of carbon tetrachloride
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-6a0d25c79e89401babe67cc26d4c68a0
Source dataset
uspto-grants-2002_10
Patent number
US06472419B1

Reaction notes

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