Water → 1-(2-Bromoethoxy)-4-(tert-butoxy)benzene

HRID 898788Notes

Reaction equation

HRID 898788 reaction equation
[OH-].[K+].[Br:3][CH2:4][CH2:5]Br.[C:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:10])([CH3:9])[CH3:8].O>CO.C(Cl)(Cl)Cl>[C:7]([O:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:5][CH2:4][Br:3])=[CH:16][CH:17]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 2773621p-Tert-butoxyphenol

Product 1

HCID 150188321-(2-Bromoethoxy)-4-(tert-butoxy)benzeneYield 29.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of KOH (0.224 g, 4 mmol) in MeOH (3 mL) was added, over the course of 30 min, to a warmed (70° C.) mixture of 1,2-dibromoethane (3 g, 0.016 mol) and 4-(tert-butoxy)phenol (0.66 g, 0.004 mol). The mixture was stirred at 70° C. for 15 h before water and CHCl3 were added. The layers were separated, the organic layer washed with 10% aqueous NaOH and then dried (Na2SO4) and concentrated in vacuo to give 0.32 g (28%) of the sub-title compound.

Workup

  1. temperatureto a warmed
  2. additionwere added
  3. customThe layers were separated
  4. washthe organic layer washed with 10% aqueous NaOH
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-088ac04fbafa4314b410de126c821bea
Source dataset
uspto-grants-2008_04
Patent number
US07351821B2

Reaction notes

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