Phosphorus tribromide → 122488-92-0

HRID 1386400Notes

Reaction equation

HRID 1386400 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH2:6]O.P(Br)(Br)[Br:13]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH2:6][Br:13]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 11744818(3-methoxy-4-methylphenyl)methanol

Product 1

HCID 18509660122488-92-0Yield 187.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 18.3 g (0.12 mol) of 3-methoxy-4-methylbenzyl alcohol in 150 mL of Et2O was treated with 23.8 g (0.12 mol) of BaCO3 and the mixture cooled in ice. This was treated dropwise with 5.8 mL (0.06 mol) of PBr3. After stirring at 0° C. for 15 minutes, the mixture was allowed to stir at room temperature overnight. The mixture was filtered and the solid washed with Et2O. The Et2O was washed with saturated NaHCO3, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 24.17 g (93.5% yield) of the product as an oil. The structure was confirmed by NMR spectroscopy.

Workup

  1. temperaturethe mixture cooled in ice
  2. stirringto stir at room temperature overnight
  3. filtrationThe mixture was filtered
  4. washthe solid washed with Et2O
  5. washThe Et2O was washed with saturated NaHCO3
  6. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-693cb2a6b60b426ca8c5a273b73f311e
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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