Diethyl Sulfate → 1,3-Dibromo-5-ethoxybenzene

HRID 1668746Notes

Reaction equation

HRID 1668746 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:20][CH3:21])(=O)=O>CC(=O)CC.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:20][CH3:21])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 122803,5-Dibromophenol

Product 1

HCID 536995421,3-Dibromo-5-ethoxybenzene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

A dispersion of 3,5-dibromophenol (0.398 g, 1.6 mmol) and potassium carbonate (0.437 g, 3.2 mmol) in 2-butanone (4 mL) was treated with diethyl sulfate (0.246 g, 1.6 mmol) and the reaction mixture heated at 90° C. for 15 hours. The resulting thick suspension was cooled to room temperature, diluted with dichloromethane and extracted with water. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The title compound was obtained as a light brown oil (0.38 g, 86% of theory) which was used in the next step without further purification.

Workup

  1. temperatureThe resulting thick suspension was cooled to room temperature
  2. extractionextracted with water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e8ad1ba1c21a4873b750436bb00270fe
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

Loading…