sulfuric acid; sodium nitrite in water; acetonitrile T=20°C; Inert atmosphere;

n-butyllithium; potassium tert-butylate; iodine in tetrahydrofuran T=-78 - 20°C; 5 h;

1: 96 percent / aq. H2SO4 / acetic acid / 16 h / Heating 2: 71 percent / NaNO2, 70percent aq. H2SO4 / 25 °C View Scheme

1: 1) lithium tetramethylpiperidide, 2) I2 / 1) THF, 2) -78 deg C 2: 96 percent / aq. H2SO4 / acetic acid / 16 h / Heating 3: 71 percent / NaNO2, 70percent aq. H2SO4 / 25 °C View Scheme