2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 118006063, compound

Participants

Reaction Steps

A solution of 29 (6.1 g, 16.3 mmol) in MeOH (6 mL) was added dropwise to a suspension of dichlorodicyanobenzoquinone (DDQ, 3.8 g, 16.7 mmol) in 80% aqueous H2SO4 (30 mL) at 0° C. After the addition was completed, the ice bath was removed and stirring was continued for 1 h. The mixture was poured in to ice water (100 mL), then the resulting brown precipitate was filtered, dissolved in ethyl acetate, and washed with H2O (100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated rotary evaporation, and purified by column chromatography to give methyl 5-bromo-7-fluoro-2-naphthoate (30) (28%). 1H NMR (600 MHz, Acetone-d6) δ 8.67 (d, J=1.3 Hz, 1H), 8.31 (d, J=8.8 Hz, 1H), 8.18-8.14 (m, 1H), 7.95 (td, J=8.7, 8.2, 2.5 Hz, 2H), 3.97 (s, 3H). GC-MS (ES) for C12H8BrFO2 [M+1]+ 283.

Provenance & Evidence