Propargyl bromide → 5-Bromo-1,2-difluoro-3-prop-2-ynyloxybenzene

HRID 2244844Notes

Reaction equation

HRID 2244844 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[CH2:11](Br)[C:12]#[CH:13].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:13][C:12]#[CH:11])[C:5]([F:9])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 27733075-Bromo-2,3-Difluorophenol

Product 1

HCID 592152525-Bromo-1,2-difluoro-3-prop-2-ynyloxybenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

50.0 g (0.24 mol) of 5-bromo-2,3-difluorophenol are refluxed for 3 h together with 32.0 ml (0.29 mol) of propargyl bromide (80% soln. in toluene) and 39.7 g (0.29 mol) of potassium carbonate in 860 ml of ethyl methyl ketone. The batch is filtered, and the filter residue is washed with MTBE. The filtrate is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:MTBE=3:1).

Workup

  1. filtrationThe batch is filtered
  2. washthe filter residue is washed with MTBE
  3. concentrationThe filtrate is concentrated to dryness
  4. customthe residue is purified by column chromatography (SiO2, n-heptane:MTBE=3:1)

Sources & evidence

ORD record
ord-bb35b0ddd6654b0c9dc938195de1d6ce
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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