PURPOSE: To high selectively produce the subject compounds in high yield at a low-temperature condition without remarkable generation of by-products by reacting a halogenobenzene represented by a specified formula with an alkalline metal fluoride in the presence of dimethylimidazolidinone.
CONSTITUTION: A halogenobenzene (e.g. 1,3,5-trichlorobenzene or 1,3-dichloro-5- bromobenzene) of formula I (X4 and X5 are Br or Cl; In case X1 and X3 are H, X2 is Br or Cl. In case X1 and X3 are Br or Cl, X2 is H) is reacted with an alkalline metal fluoride (e.g. sodium fluoride of preferably fine particle state) in the presence of 1,3-dimethylimidazolidin-2-one preferably at 225-350°C, thus obtaining the objective compounds of formula II (In case R1 and R3 are H, R2 is F. In case R1 and R3 are F, R2 is H).
KIMURA YOSHIICHI