2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10236283, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 15 (0.25 g, 0.93 mmol) and DDQ (0.42 g, 1.87 mmol) in dioxane was heated to 90° C. for 45 min. The reaction was allowed to cool and poured into 10% Na2SO3 and extracted with EtOAc. The EtOAc was dried over MgSO4, filtered and concentrated to give a yellow solid that was triturated with MeOH to give 16 as a white solid (0.050 g): Mp>300° C.; 1H NMR (DMSO d6) δ 10.88 (br s, 1H), 9.93 (br s, 1H), 8.05 (d, 1H, J=8.6 Hz), 7.77 (d, 1H, J=8.4 Hz), 7.10 (d, 1H, J=1.9 Hz), 7.05 (d, 1H, J=2.0 Hz), 7.01 (dd, 1H, J=8.6 Hz, 2.1 Hz), 6.92 (dd, 1H, J=8.4 Hz, 1.9 Hz); MS FI (neg) 267 (M−H)−.

Provenance & Evidence