2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86634834, compound

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Reaction Steps

Powdered 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (908 mg, 4.0 mmol) was added to a solution of 5 (2.033 g, 4.21 mmol) in CH2Cl2 (20 mL) at rt. After 20 minutes, the mixture was filtered through a short pad of silica gel using CH2Cl2 as the eluant. The solvent was evaporated and the residue was purified by column chromatography on silica gel (9:1 hexanes/EtOAc) to yield the title product 6 (1.65 g, 86% yield) as a solid. 1H NMR (CDCl3, 400 MHz, ppm): δ 8.03-7.93 (m, 2H), 7.54-7.12 (m, 12H), 6.86-6.79 (m, 1H), 5.04-4.94 (m, 1H), 3.29-3.06 (m, 2H); HRMS calcd for C26H19F3NO3S+1 (M+1): 482.1038. found: 482.1032.

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