Silica → 2-Methoxy-2'-amino-4,4'-dibromobiphenyl

Participants

Reaction Conditions

Reaction Steps

A solution of hydrazine hydrate (19.4 mL, 400 mmol) in ethanol (20 mL) was added dropwise into a suspension of 2-methoxy-2′-nitro-4,4′-dibromobiphenyl (15, 25.77 g, 66.59 mmol) and 5% Ru/C (2.69 g, 1.33 mmol) in ethanol (250 mL) maintained at 65-70° C. The reaction mixture was then refluxed for 7 h. The hot reaction mixture was passed through Celite 545 (1 cm thick), and the filtrate was evaporated to give an off-white powder (22.69 g, 95.46%): mp 94.5-97° C.; HPLC method 3 tR=18.57 min (97.9 area %); 1H NMR δ 3.40 (br s, 2 H), 3.80 (s, 3 H), 6.9-7.2 (m, 6 H); EI-MS m/z 355 (M+). Anal. (C13H11ONBr2) C, H, N.

Provenance & Evidence