N-bromobutanimide → 2-(Bromomethyl)-1-chloro-3-methoxybenzene

HRID 495512

Reaction equation

HRID 495512 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[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]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10][Br:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 767493-Chloro-2-methylanisole

Product 1

HCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzeneYield 72.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

442 g of 2-chloro-6-methoxytoluene are dissolved in 2420 ml of carbon tetrachloride and, together with 516 g of N-bromosuccinimide, heated at reflux for 2 h while 5.8 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. 483 g of colorless oil are obtained (b.p. 100° C./1.4 mbar, m.p. 44-47° C.).

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-13db7c02808443b4b1d3ed92957b86fe
Source dataset
uspto-grants-2005_09
Patent number
US06939888B2

Linked notes

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