2-(3-Methoxypropyloxy)-phenol → 4-Bromo-2-(3-methoxypropoxy)-phenol

HRID 744813Notes

Reaction equation

HRID 744813 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:55][O:56][CH2:57][CH2:58][CH2:59][O:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=1[OH:67]>ClCCl.CO>[Br:1][C:65]1[CH:64]=[CH:63][C:62]([OH:67])=[C:61]([O:60][CH2:59][CH2:58][CH2:57][O:56][CH3:55])[CH:66]=1

Participants

5

Reactant 2

HCID 214586242-(3-Methoxypropyloxy)-phenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 214586624-Bromo-2-(3-methoxypropoxy)-phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

6.9 g of tetrabutylammonium tribromide are added in portions, at room temperature, to a solution of 2.6 g of 2-(3-methoxypropyloxy)-phenol in 60 ml of dichloromethane and 40 ml of methanol, and the mixture is then stirred for 30 minutes. The reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and water. The combined organic phases are dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by FC (700 g of silica gel, dichloromethane/diethyl ether=98:2), yielding the title compound: Rf (dichloromethane/diethyl ether=97:3)=0.50; HPLC Rt =14.32 minutes; FAB-MS (M+H)+ =262.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is partitioned between diethyl ether and water
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is purified by FC (700 g of silica gel, dichloromethane/diethyl ether=98:2)

Sources & evidence

ORD record
ord-dd2024f6aeae42878671b730c768ddfd
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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