2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67126222, compound

Participants

Reaction Steps

A solution of 3-bromo-4-(4-chlorophenyl)-7-methoxy-2-methyl-1,2-dihydronaphthalene (5.5 g, 15.1 mmol) in toluene (100 mL) was vacuum flushed with Ar. DDQ (5.2 g, 22.7 mmol) was added and the mixture heated to reflux for 1.5 h. The heterogeneous red-brown mixture was cooled to room temperature and the toluene removed in vacuo. The resulting residue was taken up in DCM (300 mL) and filtered to remove precipitated DDHQ. The resulting mother liquor was absorbed on silica gel and purified by Yamazen column chromatography (15% DCM/Hex) to afford 5.21 g (95%) of the title compound as an amorphous yellow solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.66 (s, 1H); 7.49 (br d, J=2 Hz, 2H); 7.24-7.18 (m, 3H); 7.07 (d, J=2 Hz, 1H); 6.97 (dd, J=9.2, 2 Hz, 1H); 3.91 (s, 3H); 2.60 (s, 3H).

Provenance & Evidence