2-Methoxyphenethyl alcohol → 2-(5-Bromo-2-methoxyphenyl)ethan-1-ol

HRID 1452119Notes

Reaction equation

HRID 1452119 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH:55][CH2:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[O:64][CH3:65]>ClCCl.CO>[Br:1][C:62]1[CH:61]=[CH:60][C:59]([O:64][CH3:65])=[C:58]([CH2:57][CH2:56][OH:55])[CH:63]=1

Participants

5

Reactant 2

HCID 819092-Methoxyphenethyl alcoholHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 15020172-(5-Bromo-2-methoxyphenyl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

35.72 g of tetrabutylammonium tribromide are added in portions to a solution of 10.7 g of 2-(2-hydroxyethyl)-anisole in 195 ml of dichloromethane and 130 ml of methanol. The reaction mixture is stirred for 150 minutes at room temperature and then concentrated by evaporation using a rotary evaporator. The residue is partioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation and the residue is pudfied by means of FC (dichloromethane) to yield the title compound: Rf (dichloromethane)=0.26; HPLC Rt =13.0 minutes.

Workup

  1. concentrationconcentrated by evaporation
  2. customa rotary evaporator
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-efa0af2f5ba4469aa4fcb0fba124c16d
Source dataset
uspto-grants-1997_02
Patent number
US05606078

Reaction notes

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