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

HRID 2296985Notes

Reaction equation

HRID 2296985 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 181.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 24.4 g (0.1214 mol) of 5-bromo-2-methylbenzylalcohol in 200 ml of dry diethyl ether was added dropwise 16.4 g (0.06067 mol) of phosphorous tribromide over 30 minutes with ice-cooling. After the mixture was stirred for 3 hours with ice-cooling, the reaction mixture was added to ice water (500 ml), and the mixture was separated. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried and concentrated to obtain 29.07 g of 5-bromo-2-methylbenzylbromide as crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe mixture was separated
  4. washThe organic layer was washed successively with water
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated brine, then dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13f6ff2d94644544a90309be5b3b084d
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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