sodium hydride 1.) DMF, 0 - 5 deg C, 1 h, 2.) DMF, a) RT - 40 deg C, 2 h, b) RT, overnight; Yield given. Multistep reaction;

hydrogen bromide; acetic acid 72 h;

1: 79 percent / HBr, acetic acid / 72 h 2: 61 percent / 1N aq. NaOH / 0.75 h / Ambient temperature View Scheme

1: 79 percent / HBr, acetic acid / 72 h 2: 61 percent / 1N aq. NaOH / 0.75 h / Ambient temperature 3: 90 percent / sodium nitrite, formic acid / H2O / 0.25 h / 0 °C View Scheme