Phosphorus tribromide → HCID 12870363, compound

HRID 1463886Notes

Reaction equation

HRID 1463886 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1>C(Cl)(Cl)(Cl)Cl>[Br:2][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 19088515HCID 19088515, compound

Product 1

HCID 12870363HCID 12870363, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorus tribromide (1.42 g) was added, dropwise, to a solution of methyl 4-(2-hydroxyethyl)phenylacetate (2.7 g--see Preparation 21) in carbon tetrachloride (20 ml) at 0°. When the addition was complete, the mixture was allowed to warm to room temperature and then heated under reflux for 2 hours. Ice (100 g) was added and the mixture was partitioned between dichloromethane (50 ml) and saturated aqueous sodium bicarbonate (50 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing hexane (40%) then with dichloromethane. The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 1.02 g.

Workup

  1. customat 0°
  2. additionWhen the addition
  3. temperatureheated
  4. temperatureunder reflux for 2 hours
  5. customthe mixture was partitioned between dichloromethane (50 ml) and saturated aqueous sodium bicarbonate (50 ml)
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with dichloromethane (3×50 ml)
  8. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give an oil which
  11. customwas purified by column chromatography on silica eluting with dichloromethane
  12. additioncontaining hexane (40%)
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfa8fbb749e54e3f86002fd4d176045a
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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