Synthesis and some chemical properties of 1-aryloxy-2-chloro-1,2-difluoroethenes

A convenient method of synthesis of 1-aryloxy-2-chloro-1,2-difluoroethenes 1a-h and 1,2-di(aryloxy)-1,2-difluoroethenes 2a-d by the reaction of 1,2-dichloro-1,2-difluoroethene with substituted phenols was developed. Compounds 1a-c treated with n-C4H9Li and then with CO2 and I2 formed 3-aryloxy-2,3-difluoroacrylic acids 3a-e or 1-aryloxy-2-iodo-1,2-difluoroethenes 4a,c, respectively. Reaction of lithium derivative of 1-(4-methylphenoxy)-2-chloro-1,2-difluroethene 1c with DMF or N-formylpiperidine gave 3-(4-methylphenoxy)-3-(dimethylamino or piperidin-1-yl)-2-fluoropropenal 5c, 6c.