Phosphorus tribromide → 1-Bromo-3-(bromomethyl)-5-methoxybenzene

HRID 495981Notes

Reaction equation

HRID 495981 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5]O.P(Br)(Br)[Br:13].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][Br:13]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 10608788(3-Bromo-5-methoxyphenyl)methanol

Product 1

HCID 122764491-Bromo-3-(bromomethyl)-5-methoxybenzeneYield 214.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11 Grams (51 mmole) of 3-bromo-5methoxy benzyl alcohol was dissolved in 100 ml methylene chloride and cooled in an ice-bath. 2.0 ml (20 mmole) of phosphorus tribromide was added dropwise to this solution at room temperature, and the mixture was allowed to stir for 10 minutes. Saturated sodium bicarbonate solution was then added, and the mixture was extracted with ether and washed with sodium bicarbonate solution. Evaporation of the ether yielded 12 grams of 3-Bromo-5-methoxy-benzyl bromide as a white solid.

Workup

  1. temperaturecooled in an ice-bath
  2. extractionthe mixture was extracted with ether
  3. washwashed with sodium bicarbonate solution
  4. customEvaporation of the ether

Sources & evidence

ORD record
ord-f0122da60c774006a18680be7800c5a6
Source dataset
uspto-grants-2005_09
Patent number
US06943169B2

Reaction notes

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