Multi-step reaction with 8 steps
1: 1.) Na2S2O4, 2.) tetrabutylammonium bromide, NaOH / 1.) ether, CH2Cl2, water, 10 min, 2.) r.t., 15h
2: 88 percent / dimethylformamide / 16 h / Heating
3: 84 percent / potassium hydroxide / methanol; H2O / 72 h / Heating
4: oxalyl chloride / CH2Cl2 / 2.5 h / Ambient temperature
5: thionyl chloride / 1.) dichloromethane, r.t., 2h, 2.) r.t., 1.5h
6: 1.) Mg / 1.) THF, 2a.) 16h, r.t., 2b.) reflux, 2h
8: 90 percent / anhydrous potassium carbonate / dimethylformamide / 16 h / Ambient temperature
With
potassium hydroxide; sodium hydroxide; thionyl chloride; sodium dithionite; oxalyl dichloride; tetrabutylammomium bromide; potassium carbonate; magnesium;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/P19910000841