Ammonium Chloride → 7-Fluoro-1H-indole

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-1-nitrobenzene (20.0 g, 0.142 mol) was dissolved in dry tetrahydrofuran (400 ml) and cooled to −50° C. Vinylmagnesium chloride (288 ml, 15% wt/vol) was added at −45° C. and stirred at this temperature for 1 hr. The reaction mixture was then poured onto saturated ammonium chloride (600 ml), separated and the aqueous layer extracted with diethyl ether (2×200 ml) then dried (MgSO4), filtered and concentrated in vacuo to yield a dark oil which was purified by column chromatography on silica using toluene as mobile phase. Fractions concentrated to yield a crystalline solid. (Tetrahedron Lett. (1989), 30(16), 2129-32)

Provenance & Evidence