Phosphorus tribromide → 5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran

HRID 2253907Notes

Reaction equation

HRID 2253907 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][CH2:13][C:12]=2[CH:16]=1>C(Cl)(Cl)(Cl)Cl>[Br:2][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][CH2:13][C:12]=2[CH:16]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 212240782-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-ol

Product 1

HCID 218311605-(2-Bromoethyl)-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g-see Preparation 12) in carbon tetrachloride (3ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10% aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2×10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallised on standing, yield 0.584 g, m.p. 60°-62° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customthe mixture was partitioned between 10% aqueous sodium carbonate (20 ml) and dichloromethane (20 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×10 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c62c4b1f6e624d5dbf33f1c487a06bbe
Source dataset
uspto-grants-1993_08
Patent number
US05233053

Reaction notes

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