Diethyl Sulfate → 2-Bromophenetole

HRID 1581708Notes

Reaction equation

HRID 1581708 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-2b07609113854e9cb085baee8b98d734
Source dataset
uspto-grants-2004_05
Patent number
US06730695B2

Reaction notes

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