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

HRID 248095Notes

Reaction equation

HRID 248095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([I:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:10]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([I:9])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 28013292-Chloro-4-iodotoluene

Product 1

HCID 220586831-(Bromomethyl)-2-chloro-4-iodobenzeneYield 93.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-chloro-4-methyliodobenzene (9.0 g), N-bromosuccinimide (8.5 g), benzoyl peroxide (0.3 g) and carbon tetrachloride (80 ml) was stirred and heated to reflux for 3 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated to give 4-bromomethyl-3-chloroiodobenzene (11 g) which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-935f0674609840a5b887ec8d5a6be8ee
Source dataset
uspto-grants-1993_05
Patent number
US05208259

Reaction notes

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