Sodium Carbonate → 4-(4-Fluorophenyl)phenethyl alcohol

To a 2-5 mL microwave vial was added 2-(4-bromophenyl)ethanol (603 mg, 3.0 mmol), (4-fluorophenyl)boronic acid (462 mg, 3.3 mmol), sodium carbonate (973 mg, 9.0 mmol), palladium acetate (33.7 mg, 0.15 mmol), 1,4dioxane (4.5 mL) and water (4.5 mL). The mixture was irradiated in a CEN microwave at 120° C. for 10 minutes. The reaction mixture was biphasic upon reaction completion. The reaction mixture was extracted into ethyl acetate (2×150 mL) dried over Na2SO4 then filtered through a pad of celite. The organics were concentrated in vacuo and the crude material was purified by chromatography on silica gel (gradient: 70:30 heptanes:EtOAc). Isolated material still contained 2-(4-bromophenyl)ethanol, therefore, the material was triturated in heptanes to furnish the title compound as a white solid. (430 mg, 45%).

1. customThe mixture was irradiated in a CEN microwave at 120° C. for 10 minutes
2. customThe reaction mixture was biphasic upon reaction completion
3. extractionThe reaction mixture was extracted into ethyl acetate (2×150 mL)
4. dry with materialdried over Na2SO4
5. filtrationthen filtered through a pad of celite
6. concentrationThe organics were concentrated in vacuo
7. customthe crude material was purified by chromatography on silica gel (gradient: 70:30 heptanes:EtOAc)
8. customIsolated material still contained 2-(4-bromophenyl)ethanol, therefore, the material was triturated in heptanes

ORD-Eintrag

ord-6cb0a834f34b46cf8b228c5a983cf3cf

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853258B2