Ammonium Chloride → 5-fluoro-1-methylidene-2,3-dihydro-1H-indene-4-carbonitrile

Temperatur

-20 °C

Methyl triphenylphosphine bromide (816 mg, 2.28 mmol) was dissolved in THF (10 mL) and placed in a cool bath at −20° C. The mixture was then treated with n-butyl lithium (913 μl, 2.28 mmol), and stirred for 20 min. at −20° C. To the mixture was then added 5-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (200 mg, 1.14 mmol) via cannula and subsequently stirred for 20 min at −20° C.; LC as well as TLC (hexanes/EtOAc=1/0.3) indicated that reaction was half complete. To the mixture was poured NH4Cl, and the solution was transferred into separatory funnel, diluted with EtOAc, washed with NH4Cl, NaCl, dried over Na2SO4, filtered and concentrated to dryness. The residue was then absorbed into silica gel and separated over a silica column with the solvent systems of hexanes/EtOAc (1/0.3) to give 5-fluoro-1-methylidene-2,3-dihydro-1H-indene-4-carbonitrile. LC-MS (IE, m/z): 174 [M+1]+; tR=2.10 min.

1. customplaced in a cool bath at −20° C
2. customthe solution was transferred into separatory funnel
3. washwashed with NH4Cl, NaCl
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated to dryness
7. customThe residue was then absorbed into silica gel
8. customseparated over a silica column with the solvent systems of hexanes/EtOAc (1/0.3)

ORD-Eintrag

ord-c07df512fbe247c18bc7dd767424855c

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09018211B2