Phosphorus tribromide → 4-Bromo-2-(bromomethyl)-1-methylbenzene

HRID 1883623Notes

Reaction equation

HRID 1883623 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[CH2:7]O.P(Br)(Br)[Br:12]>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[CH2:7][Br:12]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 12993770(5-Bromo-2-methylphenyl)methanol

Product 1

HCID 129937714-Bromo-2-(bromomethyl)-1-methylbenzeneYield 181.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

24.4 g (121 mmol) of 5-bromo-2-methylbenzyl alcohol was dissolved in 200 ml of anhydrous diethyl ether, and to the resulted solution was dropped 16.4 g (60.7 mmol) of phosphorus tribromide under ice cooling. The mixture was stirred further for 3 hours under ice cooling, then, the reaction solution was poured into ice water, then, separated. The organic layer was washed with water, saturated sodium bicarbonate solution and saline sequentially, dried over anhydrous magnesium sulfate, then, concentrated to obtain 29.1 g (110 mmol) of 5-bromo-2-methylbenzyl bromide in the form of brown solid.

Workup

  1. customseparated
  2. washThe organic layer was washed with water, saturated sodium bicarbonate solution and saline sequentially
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bcaad904ed79483a845f995f03540212
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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