Phosphorus tribromide → HCID 22494096, compound

HRID 1816631Notes

Reaction equation

HRID 1816631 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Br)(Br)[Br:23]>C(COC)OC.CCOCC>[Br:23][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 22494341HCID 22494341, compound

Product 1

HCID 22494096HCID 22494096, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.2 g of ethyl 3-[3-(hydroxymethyl)-4-methoxyphenyl]-2-isopropoxypropanoate was dissolved in 15 ml dimethoxyethane. 1.2 ml phosphorus tribromide was added thereto under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction solution was diluted with ether and washed with water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was subjected to silica gel column chromatography, to give 2.6 g of ethyl 3-[3-(bromomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate from fractions eluted with hexane-ethyl acetate (4:1).

Workup

  1. temperatureunder ice-cooling
  2. washwashed with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-503ae909041e4040a24f0d42193a730b
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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