Propargyl bromide → HCID 21848312, compound

HRID 618716Notes

Reaction equation

HRID 618716 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[F:5][C:6]1[C:7]([CH2:13][CH2:14][CH3:15])=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:3][C:2]#[CH:1])[C:7]=1[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 21848298HCID 21848298, compound

Product 1

HCID 21848312HCID 21848312, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.4 g (11.7 mmol) of propargyl bromide in 1 ml of dimethylformamide was added dropwise to a suspension of 1.3 g (8.4 mmol) of 3-fluoro-2-propyl-phenol and 1.7 g of potassium carbonate in 4 ml of dimethylformamide and the mixture was subsequently stirred at room temperature for one hour. The mixture was poured on to 30 ml of ice-water and extracted three times with 50 ml of dichloromethane each time. After drying concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane/hexane 1:1). There were obtained 1.45 g (90%) of 1-fluoro-2-propyl-3-prop-2-ynyloxy-benzene as a pale yellow oil.

Workup

  1. extractionextracted three times with 50 ml of dichloromethane each time
  2. customAfter drying
  3. concentrationconcentration
  4. customThe crude product obtained
  5. customwas purified by column chromatography on silica gel (dichloromethane/hexane 1:1)

Sources & evidence

ORD record
ord-59a7f323e19143b5953e2ad0beee40b0
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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