2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11196232, compound

Participants

Reaction Conditions

Reaction Steps

To a 1 L 3-neck flask fitted with an addition funnel, N2 inlet, magnetic stir bar and thermometer was added 15.26 (0.067 mol) of 3,4-dichloro-bromobenzene in 50-75 mL of anhydrous ether. The reaction was cooled to −90° C. and 96 mL of tert-butyllithium (1.7 M solution in pentane) slowly was added over a 0.5 hr while maintaining the temperature below −70° C. The reaction temperature was cooled to −80 to −90° C. and 2-chloropyrimidine (9.10 gm, 0.08 mol) dissolved in anhydrous THF was added. The reaction was stirred for about 2 h and 18 gms of DDQ, (0.077 mol) dissolved in anhydrous THF was added slowly, and the mixture was stirred for a 0.5 h. Three mL of H2O containing 1 mL of HOAc in THF was added and the mixture stirred for 15 minutes. The reaction was diluted with 100 mL of H2O and 100 mL of EtOAc and the mixture transferred to a separatory funnel. The organic layer was separated, dried, filtered and evaporated. The crude product was chromatographed and eluted with 30% EtOAc/heptane and triturated with Et2O to yield 3.22 g of a white solid (20%) m.p. 126-127° C.

Provenance & Evidence