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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence