2,5 Dibromotoluene → 1,4-Dibromo-2-(bromomethyl)benzene

HRID 865324Notes

Reaction equation

HRID 865324 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH3:9].[Br:10]Br>[W]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][Br:10]

Participants

4

Conditions

Temperature
150 °C

Procedure

33 g (0.1 mole) 2,5-dibromo toluene is placed in a 100 ml three-necked flask, fitted with a reflux condenser, a sealed mechanical stirrer, and a separatory funnel with the stem reaching nearly to the bottom of the flask. The flask is illuminated with two 300-watt tungsten lamps during the reaction. The flask is heated in an oil bath to 150° C., and 18.4 g (5.9 ml, 0.115 mole) bromine is added over two hours. The mixture is stirred for an additional 10 minutes, and the contents, while still liquid, are poured into a 500 ml round-bottom flask containing 300 ml of hot light petroleum ether and 2 g decolorizing carbon. A reflux condenser is attached, and the mixture is heated to reflux until the material dissolves, then rapidly filtered through a pre-heated Buchner funnel. The filtrate is cooled and washed with cold light petroleum.

Workup

  1. customfitted with a reflux condenser, a sealed mechanical stirrer, and a separatory funnel with the stem
  2. additionthe contents, while still liquid, are poured into a 500 ml round-bottom flask
  3. customA reflux condenser is attached
  4. temperaturethe mixture is heated
  5. temperatureto reflux until the material
  6. dissolutiondissolves
  7. filtrationrapidly filtered through a pre-heated Buchner funnel
  8. temperatureThe filtrate is cooled
  9. washwashed with cold light petroleum

Sources & evidence

ORD record
ord-06440eaa704a44ab983435d709b78aca
Source dataset
uspto-grants-1996_10
Patent number
US05565543

Reaction notes

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