PURPOSE: To obtain a fluorine-containing p-chlorophenylcarbamic acid ester useful as an intermediate for agricultural chemicals, dyes, pigments, liquid crystals and pharmaceuticals, especially herbicides having high activity from an easily available industrial raw material with simple process.
CONSTITUTION: The objective compound of formula II can be produced at a low cost by chlorinating a phenylcarbamic acid ester of formula I (R is H, 1-4C alkyl or alkyl, alkenyl, alkynyl or cycloalkyl which may be substituted with halogen atom, etc.; R' is lower alkyl) with a chlorination agent such as gaseous chlorine, sulfuryl chloride, N-chlorosuccinimide and Cu (II) chloride at -20 to +150°C (preferably room temperature to 120°C) in a solvent or in the absence of solvent preferably in the presence of a catalytic amount of a base. The starting compound of formula I is obtained by converting a compound of formula III to a diazonium salt under acidic condition, hydrolyzing the salt and reacting the resultant compound of formula IV with a compound of the formula R-Y (Y is halogen, etc.) in a proper solvent in the presence of a base.
ONCHI YUICHI
SATO KOJI
HIROSE HIROAKI
