Diethyl Sulfate → 2-Bromophenetole

HRID 983517Notes

Reaction equation

HRID 983517 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 sulphate 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-0712c5114dfc483784435abdf4cff346
Source dataset
uspto-grants-2005_03
Patent number
US06864277B2

Reaction notes

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