Phosphorus tribromide → 3,4-Methylenedioxyphenethyl bromide

HRID 375577Notes

Reaction equation

HRID 375577 reaction equation
P(Br)(Br)[Br:2].[CH2:5]1[O:16][C:15]2[CH:14]=[CH:13][C:9]([CH2:10][CH2:11]O)=[CH:8][C:7]=2[O:6]1>C(Cl)(Cl)(Cl)Cl>[CH2:5]1[O:16][C:15]2[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][Br:2])=[CH:8][C:7]=2[O:6]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol

Product 1

HCID 122072243,4-Methylenedioxyphenethyl bromideYield 121.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of phosphorus tribromide (8.1 g) in carbon tetrachloride (50 ml) was added dropwise over 30 minutes to a stirred solution of 3,4-methylenedioxyphenethyl alcohol (15.0 g) (see Preparation 5) in carbon tetrachloride (200 ml) and the mixture was heated under reflux for 3 hours, washed sequentially with water (twice), 5M aqueous sodium hydroxide solution and water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (100 g) using carbon tetrachloride as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a pale yellow oil (8.3 g, 40%), which was characterised by its 1H-NMR spectrum.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washwashed sequentially with water (twice), 5M aqueous sodium hydroxide solution and water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (100 g)
  7. customevaporated

Sources & evidence

ORD record
ord-d8498382db174ecc82a5bba16c88d659
Source dataset
uspto-grants-1996_01
Patent number
US05486527

Reaction notes

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