1: 27 percent / AlCl3 / 1,2-dichloro-ethane / 4.5 h / 20 °C 2: diethyl ether; toluene / 3 h / Ambient temperature 3: K2CO3 / methanol; H2O / 6 h / Heating 4: 95 percent / red phosphorus, I2 / aq. acetic acid / 5 h / Heating 5: SOCl2 / hexane / 4 h / Heating 6: NH3 / diethyl ether / Ambient temperature View Scheme

1: 1.) aq. HCl, NaNO2 / 1.) water, 0 deg C, 45 min, 2.) ethyl acetate, 55 deg C, 30 min 2: KOH / ethanol; H2O / 12 h / Heating 3: 1.) K2CO3, 2.) NaOH / 1.) DMF, 60 deg C, 5 h, 2.) ethanol/water, reflux, 5.5 h 4: SOCl2 / hexane / 4 h / Heating 5: NH3 / diethyl ether / Ambient temperature View Scheme

1: 1.) K2CO3, 2.) NaOH / 1.) DMF, 60 deg C, 5 h, 2.) ethanol/water, reflux, 5.5 h 2: SOCl2 / hexane / 4 h / Heating 3: NH3 / diethyl ether / Ambient temperature View Scheme

1: SOCl2 / hexane / 4 h / Heating 2: NH3 / diethyl ether / Ambient temperature View Scheme

1: diethyl ether; toluene / 3 h / Ambient temperature 2: K2CO3 / methanol; H2O / 6 h / Heating 3: 95 percent / red phosphorus, I2 / aq. acetic acid / 5 h / Heating 4: SOCl2 / hexane / 4 h / Heating 5: NH3 / diethyl ether / Ambient temperature View Scheme

1: 95 percent / red phosphorus, I2 / aq. acetic acid / 5 h / Heating 2: SOCl2 / hexane / 4 h / Heating 3: NH3 / diethyl ether / Ambient temperature View Scheme