Hydrochloric Acid → 3-(4-Fluorophenyl)prop-2-yn-1-ol

A solution of 4-fluoro-1-iodobenzene (11.0 g, 50.0 mmol) in anhydrous tetrahydrofuran (90 mL) was degassed and copper(I) iodide (0.29 g, 1.5 mmol), tetrakis(triphenylphosphine)palladium (1.75 g, 1.5 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (9.25 g, 60.0 mmol) were added. The reaction solution was degassed again and propargyl alcohol (3.5 mL, 60.0 mmol) was added dropwise under inert atmosphere at ambient temperature. The obtained yellow suspension was stirred at ambient temperature overnight, then treated with brine (10 mL) and acidified with 2 M hydrochloric acid to pH˜2. The phases were separated and the aqueous phase was extracted with ether (4×50 mL). The combined organic phases were washed with water (3×30 mL) and brine (2×30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo yielding brown solid. The residue was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 90:10) and the obtained light yellow solid was crystallized from hexane yielding 3-(4-fluorophenyl)prop-2-yn-1-ol as light yellow needles.

1. customThe reaction solution was degassed again
2. customThe phases were separated
3. extractionthe aqueous phase was extracted with ether (4×50 mL)
4. washThe combined organic phases were washed with water (3×30 mL) and brine (2×30 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated in vacuo
7. customyielding brown solid
8. customThe residue was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 90:10)
9. customthe obtained light yellow solid was crystallized from hexane

ORD record

ord-0daf22f62fa14280aa21db04cb8c7431

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551993B2