thionyl chloride in chloroform RefluxCooling with ice;

1: p-hydroxybenzaldehyde hydrochloride With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.5 h; 2: 1-chloro-2-(perhydroazepin-1-yl)ethane hydrochloride With potassium carbonate in N,N-dimethyl-formamide 1 h;

1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / Reflux 2: hydrogenchloride / dichloromethane / 25 - 35 °C / Inert atmosphere View Scheme

sodium hydroxide; tetrabutylammomium bromide in water; toluene Reflux;

hydrogen fluoride T=6 - 13°C; 5.08333 h; electrochemical fluorination;

1.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / Reflux 2.1: hydrogenchloride / dichloromethane / 25 - 35 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C 3.2: 5 °C 4.1: hydrogen / palladium 10 on activated carbon / water; acetone; methanol / 40 °C / 7355.72 Torr View Scheme

hydrogen fluoride T=6 - 13°C; 5.08333 h; electrochemical fluorination;

sodium azide in water T=80°C;

1.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / Reflux 2.1: hydrogenchloride / dichloromethane / 25 - 35 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C 3.2: 5 °C View Scheme