1: 1) NaNO2/HCl, 2) KI, I2 / acetic acid, H2O, 1) 45 min., 2) 2.1) < 10 deg C, 2.5 h, 2.2) RT, overnight 2: 81 percent / KOH / aq. ethanol / Heating View Scheme

(i) NaNO2, aq. HCl, (ii) /BRN= 3587244/; Multistep reaction;