trichlorophosphate in N,N-dimethyl-formamide T=110°C; 0.333333 h; Microwave irradiation;

1: potassium carbonate; iodine / H2O / 13 h / 20 - 50 °C 2: POCl3 / dimethylformamide / 2.5 h / 80 °C View Scheme

1: 73 percent / KOH / 2-methyl-propan-2-ol / 10 h / Heating 2: potassium carbonate; iodine / H2O / 13 h / 20 - 50 °C 3: POCl3 / dimethylformamide / 2.5 h / 80 °C View Scheme

1: 2-chloro-5-iodo-3-trifluoromethylpyridine With n-butyllithium in tetrahydrofuran; hexane; toluene T=-78°C; 1.66667 h; 2: formic acid ethyl ester in tetrahydrofuran; hexane; toluene 1.66667 h;

1: sodium t-butanolate / 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 2 h / Inert atmosphere; Reflux 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 0.5 h / 170 °C / Reflux; Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 3 h / 20 °C View Scheme