3'-Bromoacetophenone → (R,E)-N-(1-(3-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

Add Ti(OEt)4 (7 mL, 17 mmol) to a solution of (R)-(+)-2-methyl-2-propane sulfinamide (1.0 g, 8.3 mmol) and 1-(3-bromophenyl)ethanone (1.8 g, 9.1 mmol) in anhydrous THF (30 mL) at RT. Heat the mixture at 70° C. for 24 h. Allow the reaction mixture to cool to RT and pour into 30 mL of brine under vigorous stirring. Filter the suspension through a pad of Celite and wash the solid with EtOAc (2×20 mL). Wash the filtrate with brine (30 mL), dry (Na2SO4), and concentrate in vacuo. Chromatograph the residue on a silica gel column and elute with Et2O/hexanes to give (R)—N-(1-(3-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide.

Provenance & Evidence