Propargyl alcohol → 3-(3-fluorophenyl)prop-2-yn-1-ol

HRID 889001Notes

Reaction equation

HRID 889001 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[F:5][C:6]1[CH:7]=[C:8](I)[CH:9]=[CH:10][CH:11]=1>[Cu](I)I.C(NCC)C>[F:5][C:6]1[CH:11]=[C:10]([C:3]#[C:2][CH2:1][OH:4])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 707251-Fluoro-3-iodobenzene

Product 1

HCID 27826973-(3-fluorophenyl)prop-2-yn-1-olYield 93%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8021DiethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of propargyl alcohol (0.200 g, 5.4 mmol), 3-fluoro iodobenzene (0.63 ml, 5.4 mmol), copper iodide (0.103 g, 0.54 mol), dichlorobis (triphenylphosphine) palladium (II) (0.190 g, 0.3 mmol), diethylamine (10 ml) was degassed for 10 min. and stirred for 20 hrs at 25-25° C. Excess of diethyl amine was distilled off under vacuum. The residue was diluted with water (10 ml) and extracted with ethyl acetate. The organic layer was washed with brine solution and dried over Na2SO4. The solvent was evaporated and the crude product was purified by column chromatography (10% Ethyl acetate in hexane) to obtain pure 3-(3-fluoro-phenyl)-prop-2-yn-1-ol (0.750 g, 93%).

Workup

  1. customwas degassed for 10 min.
  2. distillationExcess of diethyl amine was distilled off under vacuum
  3. additionThe residue was diluted with water (10 ml)
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. customthe crude product was purified by column chromatography (10% Ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b4b81e05f590466c97e4a268ba559317
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

Loading…