Exploring the nitro group reduction in low-solubility oligo-phenylenevinylene systems: Rapid synthesis of amino derivatives

Trifluoromethanesulfonic Acid Promoted Controllable Electrophilic Aromatic Nitration

“…Using general procedure A, 1,4-dibromobenzene (236 mg, 1 mmol) was used as the substrate. Compound 2j was isolated as a white solid (279 mg, 99% yield) after flash chromatography (20/1 petroleum ether/ethyl acetate): 1 H NMR (400 MHz, CDCl 3 ) δ 7.95 (s, 1H), 7.59 (d, J = 6.1 Hz, 1H), 7.54 (d, J = 8.5 Hz, 1H); 13 C­{ 1 H} NMR (101 MHz, CDCl 3 ) δ 150.1, 136.3, 136.2, 128.5, 121.5, 113.3 …”

“…Compound 2j was isolated as a white solid (279 mg, 99% yield) after flash chromatography (20/1 petroleum ether/ethyl acetate): 1 H NMR (400 MHz, CDCl 3 ) δ 7.95 (s, 1H), 7.59 (d, J = 6.1 Hz, 1H), 7.54 (d, J = 8.5 Hz, 1H); 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 150.1, 136.3, 136.2, 128.5, 121.5, 113.3. 21 Ethyl 2-(4-Chloro-2-nitro-phenoxy)-2-methylpropionate 2k. Using general procedure A, clofibrate (213 μL, 1 mmol) was used as the substrate.…”