Production of polyhalogenated cinnamic acid derivatives useful as intermediates in producing indanone derivatives, involves reacting diazonium salt with acrylic acid compound in presence of palladium catalyst

摘要

Production of polyhalogenated cinnamic acid derivatives (I) involves reacting a diazonium salt (II) with an acrylic acid compound (III) in the presence of a homogeneous palladium catalyst at -5 to +100 deg C. Production of polyhalogenated cinnamic acid derivatives of formula (I) involves reacting a diazonium salt of formula (II) with an acrylic acid compound of formula (III) in the presence of a homogeneous palladium catalyst at -5 to +100 deg C. R1-R4 = H, F, Cl or Br, at least two being other than H; X = OR5 or NR6R7; R5 = H, optionally substituted 1-10C alkyl, optionally substituted phenyl or benzyl; R6, R7 = optionally substituted 1-10C alkyl; R8 = H, Cl, Br or optionally substituted 1-10C alkyl; A- = halide, bisulfate, nitrate, acetate, tetrafluoroborate, sulfate or phosphate. Independent claims are also included for the following: (1) Process for preparing indanone derivatives of formula (IVa), involves hydrogenating compound (I) and cyclizing the product; and (2) Process for preparing indanone derivatives of formula (IVb), involves preparing a compound (IVa) as in (1), halogenating the product if R8 is hydrogen, and subjecting the product to palladium-catalyzed carbonylation with carbon monoxide and a nucleophile. R9 = COOH, CONH2 or COOR10; and R10 = 1-4C alkyl.