Methanol → 2-Methoxy-2'-nitro-4,4'-dibromobiphenyl

Participants

Reaction Steps

A solution of sodium methoxide in methanol (22.7 mL, 99.4 mmol) was added dropwise to a solution of 4,4′-dibromo-2,2′-dinitrobiphenyl (14, 33.28 g, 82.79 mmol) in DMF (250 mL) cooled in ice-bath. The reaction mixture was stirred overnight at room temperature under N2. The reaction mixture was then poured into ice-water (700 mL). The precipitated solid was collected and recrystallized from acetonitrile (200 mL) and methanol (100 mL) to give an olive green crystal (18.88 g, 59.0%): mp 127-129° C.; HPLC method 3 tR=9.57 min (96.5 area %); 1H NMR (400 MHz, CDCl3) δ 3.69 (s, 3 H), 7.04 (d, J=1.6 Hz, 1 H), 7.14 (d, J=8.1 Hz, 1 H), 7.23 (dd, J1=1.6 Hz, J2=7.3 Hz, 1 H), 7.26 (d, J=7.3 Hz, 1 H), 7.76 (dd, J1=1.9 Hz, J2=8.1 Hz, 1 H), 8.09 (d, J=1.9 Hz, 1 H); EI-MS m/z 385 (M+). Anal. (C13H9O3NBr2) C, H, N.

Provenance & Evidence