Propargyl bromide → 1,2-Difluoro-3-prop-2-ynyloxybenzene

HRID 1873302Notes

Reaction equation

HRID 1873302 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10](Br)[C:11]#[CH:12].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[F:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:9][CH2:12][C:11]#[CH:10])[C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 808792,3-Difluorophenol

Product 1

HCID 592152381,2-Difluoro-3-prop-2-ynyloxybenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

115.0 g (0.88 mol) of 2,3-difluorophenol are refluxed for 3 h in 1.6 l of ethyl methyl ketone together with 118.2 ml (17.7 mol) of propargyl bromide (80% soln. in toluene) and 146.6 g (138.2 mol) of potassium carbonate. The batch is filtered, and the filter residue is washed with MTBE. The filtrate is evaporated 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. customThe filtrate is evaporated to dryness
  4. customthe residue is purified by column chromatography (SiO2, n-heptane:MTBE=3:1)

Sources & evidence

ORD record
ord-1534a6585e12484da63b7f5d73c818ae
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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