2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86694693, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-nitro-1H-benzo[d]imidazole-1-carboxylate (150 g, 0.56 mol) in dry THF (1500 mL) was added EtMgBr (3.0 Min THF, 1.12 mol, 2 equiv.) dropwise at −15° C. The reaction mixture was stirred at −15° C. for 2 h. A solution of DDQ (129 g, 1.12 mol, 2 equiv.) in THF (120 mL) was added at −15° C., then the reaction mixture was warmed to RT and the stirring was continued for 2 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with brine and then (Na2SO4), filtered, and concentrated. The crude material was purified by SiO2 chromatography eluting with 10% EtOAc/hexane to afford tert-butyl 4-ethyl-5-nitro-1H-benzo[d]imidazole-1-carboxylate (20 g, 12% yield) as a yellow solid.

Provenance & Evidence