2,4-Dichlorotoluene → 5-Bromo-2,4-dichlorotoluene

HRID 326178

Reaction equation

HRID 326178 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Cl-].[Al+3].[Cl-].[Cl-].[Br:14]Br>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Br:14])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 3

HCID 72542,4-DichlorotolueneHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 204627725-Bromo-2,4-dichlorotoluene

Procedure

500 parts of 2,4-dichlorotoluene (b.p.=198° to 200° C.) and 10 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. 397 parts of bromine was added dropwisely at 30° to 40° C. over a period of 5 hours. The reaction liquid was washed with warm water followed by separating the water layer, and then the oil layer was cooled. The separated crystals were filtered off, recrystallized from methanol to obtain 295 parts of 2,4-dichloro-5-bromotoluene having a melting point of 82.5° to 84.0° C.

Workup

  1. customprovided with a reflux condenser
  2. customThe reaction liquid
  3. washwas washed with warm water
  4. customby separating the water layer
  5. temperaturethe oil layer was cooled
  6. filtrationThe separated crystals were filtered off
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-1b4b73c2a2624b469563fe3b1ae542f6
Source dataset
uspto-grants-1984_04
Patent number
US04444983

Linked notes

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