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

HRID 993225Notes

Reaction equation

HRID 993225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[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][C:5]([CH2:8][Br:11])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2928585-CHLORO-2-METHYLANISOLE

Product 1

HCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzeneYield 67.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

303 g of 4-chloro-2-methoxytoluene are dissolved in 1665 ml of carbon tetrachloride and, together with 355 g of N-bromosuccinimide, heated at reflux for 2 h while 4.0 g of AIBN are added. The solid is filtered off and wasted with a small amount of carbon tetrachloride, the filtrate is concentrated, and the residue which remains is fractionated. 307 g of colorless oil are obtained (b.p. 103° C./1.5 mbar, m.p. 42-45° C.).

Workup

  1. temperatureheated
  2. additionare added
  3. filtrationThe solid is filtered off
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-4c5e4fb02c15435a9eac5a793da737ea
Source dataset
uspto-grants-2002_10
Patent number
US06472419B1

Reaction notes

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