Diethyl Sulfate → 2-Bromophenetole

HRID 1593400Notes

Reaction equation

HRID 1593400 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].S(OCC)(O[CH2:13][CH3:14])(=O)=O>[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 6163Diethyl SulfateHCID 72442-Bromophenol

Product 1

HCID 685002-Bromophenetole

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 17.5 g of 2-bromophenol, 66 ml of diethyl sulfate and 170 ml of 10% NaOH solution is refluxed for 2 hours. After cooling the reaction mixture to RT, it is extracted with EtOAc, the organic phase is washed with 2N NaOH solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 19.6 g of the expected product are obtained.

Workup

  1. temperatureis refluxed for 2 hours
  2. extractionit is extracted with EtOAc
  3. washthe organic phase is washed with 2N NaOH solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-1dba9929ca8d4ca5997d67838bc04df7
Source dataset
uspto-grants-2007_11
Patent number
US07297692B2

Reaction notes

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