Bromine → 1-Bromo-4-chloro-2,5-dimethylbenzene

HRID 326179

Reaction equation

HRID 326179 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Cl-].[Al+3].[Cl-].[Cl-].[Br:14]Br>O>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:14])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 24408BromineHCID 32883Chloro-p-xyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 180041871-Bromo-4-chloro-2,5-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

400 parts of 2-chloro-p-xylene (b.p.=183° to 184° C.) and 2 parts of anhydrous aluminum chloride were charged into a 1-liter four-necked flask provided with a reflux condenser, a thermometer, a stirrer and a dropping funnel, to which 360 parts of bromine was dropwisely added over a period of 5 hours to carry out the reaction at 35° to 60° C. Water was added to the reaction liquid to wash the same with the thus added water and to remove the catalyst, and then the oil layer was cooled. The separated crystals were filtered, and washed with methanol to obtain 377 parts of 2-chloro-5-bromo-p-xylene having a melting point of 60° to 64° C.

Workup

  1. customprovided with a reflux condenser
  2. customthe reaction at 35° to 60° C
  3. washto wash the same with the thus added water
  4. customto remove the catalyst
  5. temperaturethe oil layer was cooled
  6. filtrationThe separated crystals were filtered
  7. washwashed with methanol

Sources & evidence

ORD record
ord-f2c409d37d204f90b69cc7d1b4cfa72c
Source dataset
uspto-grants-1984_04
Patent number
US04444983

Linked notes

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