Sodium Dithionite → HCID 68487875, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydrosulfite (37.7 g, 216 mmol) dissolved in water (200 mL) was added dropwise to a vigorously stirred solution of 2-[(3-bromo-5-chlorophenyl)oxy]-3-fluoro-4-methyl-1-nitrobenzene (13.0 g, 36.1 mmol) dissolved in THF (100 mL). The reaction was stirred for 16 h at 40° C. The layers were separated and the aqueous phase was extracted with EtOAc (2×100 mL). The organic extracts were combined, dried over Na2SO4, filtered and concentrated. The crude oil was purified by column chromatography (5% to 100% EtOAc/hexanes gradient) to afford the title compound (5.0 g, 42%) as a light tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.39-7.38 (m, 1H), 6.98-6.97 (m, 1H), 6.90-6.85 (m, 2H), 6.54-6.52 (m, 1H), 2.08 (s, 3H).

Provenance & Evidence