Phosphorus tribromide → 1-(Bromomethyl)-2,4-dimethylbenzene

HRID 1159643

Reaction equation

HRID 1159643 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:9]O.P(Br)(Br)[Br:12]>CCOCC>[Br:12][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 278092,4-Dimethylbenzyl alcohol

Product 1

HCID 27346041-(Bromomethyl)-2,4-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

5 g of (2,4-dimethylphenyl)methanol are dissolved in 100 ml of ether. The reaction mixture is cooled to 0° C. It is admixed dropwise with 5.2 ml of phosphorus tribromide. It is stirred at ambient temperature overnight. The reaction mixture is poured onto ice and extracted with AcOEt. The organic phase is washed with saturated NaCl solution. The organic phase is dried over MgSO4, filtered and evaporated to dryness. This gives 7.3 g of the expected compound.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted with AcOEt
  3. washThe organic phase is washed with saturated NaCl solution
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d73d118dd0614b2d8413423dd397717a
Source dataset
uspto-grants-2010_10
Patent number
US07812165B2

Linked notes

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