1: 1.) SOCl2; 2.) NaN3 in water, tetrabutylammonium bromide / 1.) methylene dichloride; 2.) 0 deg C, 2 h 2: 1.) trifluoroacetic acid; 2.) K2CO3 / 1.) CHCl2, reflux, 6 h; 2.) aq. methanol, 20 h View Scheme

oxalyl dichloride in dichloromethane

Multi-step reaction with 5 steps 1: 1.) SOCl2; 2.) NaN3 in water, tetrabutylammonium bromide / 1.) methylene dichloride; 2.) 0 deg C, 2 h2: 1.) trifluoroacetic acid; 2.) K2CO3 / 1.) CHCl2, reflux, 6 h; 2.) aq. methanol, 20 h3: 75 percent / NBS / dimethylformamide / 24 h4: 1.) conc. HCl, aq. NaNO2; 2.) 50percent H3PO3 / 1.) acetic anhydride; 2.) 0 deg C, 1 h5: 1.) BuLi / 1.) ether, 0 deg C; 2.) reflux, 5 h  

With  thionyl chloride; sodium azide; tetrabutylammomium bromide  1.) methylene dichloride; 2.) 0 deg C, 2 h;  Yield given. Multistep reaction;