Dimethylformamide → 5-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

Temperatur

-78 °C

A solution of 6-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin (146 mg, 0.627 mmol) in THF (5 ml) at −78° C. was treated with n-BuLi (0.551 ml, 1.378 mmol) under a nitrogen atmosphere and stirred at −78° C. for 15 min before treatment with a solution of DMF (0.243 ml, 3.13 mmol) in THF) (2.00 ml). The reaction was stirred for 10 min at −78° C. and then the reaction was allowed warm to rt over 10 min and stirred at rt for 0.5 h. Reaction was treated with 2M HCl (20 ml) and extracted with ethyl acetate (3×100 ml). The organic extracts were evaporated, dried (MgSO4), filtered, evaporated, chromatographed (0-100% EtOAC:Cyclohexane) to give product as a white solid (25 mg, 22%).

1. temperaturethe reaction was allowed warm to rt over 10 min
2. stirringstirred at rt for 0.5 h
3. customReaction
4. extractionextracted with ethyl acetate (3×100 ml)
5. customThe organic extracts were evaporated
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customchromatographed (0-100% EtOAC:Cyclohexane)

ORD-Eintrag

ord-6c56a9e2edb34fceaa0c6566e8b08525

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08389524B2