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

HRID 1608796Notes

Reaction equation

HRID 1608796 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 5) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10% aqueous sodium carbonate solution (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulphate and evaporated 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 solution (20 ml) and dichloromethane (20 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. dry with materialThe combined dichloromethane extracts were dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-2402eadee7314d2797a564d444fac653
Source dataset
uspto-grants-1995_03
Patent number
US05397800

Reaction notes

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