Propargyl alcohol → 3-(4-Fluorophenyl)prop-2-yn-1-ol

To a mixture of 4-fluoroiodobenzene (710.0 mg, 3.82 mmol), bistriphenylphosphine palladium chloride (27.0 mg, 0.038 mmol), CuI (3.64 mg, 0.019 mmol) and propargyl alcohol (214.0 mg, 3.82 mmol), was added diisopropylamine (6.1 mL, 1.6 mL/mmol) under nitrogen atmosphere. The reaction mixture was stirred at r.t. for 6 h. After the completion of the reaction as confirmed by TLC, the crude product was extracted with ethylacetate (50 mL). The organic layer was washed with 10% HCl (20 mL), dried over Na2SO4 and concentrated in vacuo to afford the crude compound which was purified by column chromatography (silica gel, 2:8 EtOAc:Pet.Ether) to afford 3-(4-fluoro-phenyl)-prop-2-yn-1-ol (366.0 mg, 64%) as a viscous oil.

1. customAfter the completion of the reaction
2. extractionthe crude product was extracted with ethylacetate (50 mL)
3. washThe organic layer was washed with 10% HCl (20 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customto afford the crude compound which
7. customwas purified by column chromatography (silica gel, 2:8 EtOAc:Pet.Ether)

ORD record

ord-4f4dbbfb635946ccbf5f9a823df32f63

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455479B2