Benzyl amide → HCID 14789753, compound

Participants

Reaction Conditions

Reaction Steps

Titanium tetrachloride (0.127 mol, 127 mL of a 1.0 M methylene chloride solution) was added dropwise over a 15 minute to a mechanically stirred suspension of 2,7-difluoro-4-methoxyfluorenone (I) (50.0 g, 0.203 mol) and benzylamide (81 g, 0.76 mol) in methylene chloride (1 L) under nitrogen, keeping the temperature below 15° C. The mixture was stirred for 30 min while warming to 24° C., and then filtered through a pad of Florisil, washing with diethyl ether (4 L). The filtrate was concentrated to 500 mL and diluted with hexane (500 mL). The precipitated yellow imine was collected by filtration and combined with second and third crops obtained by concentration of the mother liquor to provide a total of 64 g (94%) of (II) as mixture of geometric isomers: IR (KBr) 1648, 1617, 1603, 1592, 1469, 1452, 1321, 1294 cm-1 ; 1H NMR (CDCl3, 200 MHz)δ7.95-6.40 (m, 10 H), 5.26 and 5.27 (singlets, total 2 H), 3.94 and 3.96 (singlets, total 6 H).

Provenance & Evidence