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

HRID 269441Notes

Reaction equation

HRID 269441 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:5]=[C:6]([CH3:11])[C:7]([Br:10])=[CH:8][CH:9]=1>>[Br:3][C:4]1[CH:5]=[C:6]([C:7]([Br:10])=[CH:8][CH:9]=1)[CH2:11][Br:1]

Participants

3

Reactant 2

HCID 120062,5 DibromotolueneHCID 24408Bromine

Product 1

HCID 53260381,4-Dibromo-2-(bromomethyl)benzene

Procedure

In a three-necked round-bottom 250 ml flask equipped with a reflux condenser, thermometer, dropping funnel with pressure-equalizing, and magnetic stirring bar 15.5 ml (47.9 g, 0.30 mmol) of bromine were added dropwise to 74.9 g (0.30 mol) of 3,6-dibromotoluene under exposure to 500 W lamp for 3 h at 190° C. The resulting mixture was cooled to room temperature. Fractional distillation gave a colorless liquid, b.p. 132-135° C./3 mm Hg. Yield 84.3 g (85%).

Workup

  1. customIn a three-necked round-bottom 250 ml flask equipped with a reflux condenser
  2. distillationFractional distillation
  3. customgave a colorless liquid, b.p. 132-135° C./3 mm Hg

Sources & evidence

ORD record
ord-096916b32c1f4d6e911b1d588ec88e12
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Reaction notes

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