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

HRID 264916Notes

Reaction equation

HRID 264916 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 is then concentrated by evaporation in a rotary evaporator. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (dichloromethane), yielding the title compound: Rf (dichloromethane)=0.26; HPLC Rt =13.04 minutes.

Workup

  1. concentrationis then concentrated by evaporation in a rotary evaporator
  2. customThe residue is partitioned between diethyl ether and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is purified by means of FC (dichloromethane)

Sources & evidence

ORD record
ord-73fe6bf9dfdd47c4b24a39ac196b7dd3
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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