2-Bromophenol → 2-bromophenyl propargyl ether

HRID 552073Notes

Reaction equation

HRID 552073 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9](Br)[C:10]#[CH:11].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH2:11]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:10]#[CH:9]

Participants

6

Reactant 4

HCID 72442-BromophenolHCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 109875512-bromophenyl propargyl etherYield 106.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-bromophenol (6.12 g, 35.3 mmol) and propargyl bromide (5.67 g, 38.1 mmol) were dissolved in DMF (34 ml). This solution was added with potassium carbonate (10.9 g, 78.9 mmol) and stirred at room temperature for 14 hours. The reaction solution was added with ethyl acetate, sequentially washed with water and saturated sodium chloride water, and dried with anhydrous sodium sulfate. Concentration under reduced pressure was carried out to obtain the title compound (7.91 g, 98.0%) as a yellow oily product.

Workup

  1. washsequentially washed with water and saturated sodium chloride water
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-d036a0fece9d423588dcd998e73aaeda
Source dataset
uspto-grants-2011_05
Patent number
US07951799B2

Reaction notes

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