| 摘要 |
Aromatic compounds containing a halogen atom ortho to a CO2H, COCl, CN, CHCl2 or CRCl2 group (R = C1- 5 alkyl) are prepared by reacting aromatic compounds containing a halogen atom or nitro group ortho to a CH2R1 (CH3, CH2Cl or CH2R) group, with Cl2 in presence of a mixture of hetero-aromatic nitrogen base and an amount of P compound not more than 0.05 mole per mole starting material for each CH2R1 group present. In Examples, (1) 6-chloro-2-nitrotoluene is chlorinated in presence of a mixture of pyridine with H3PO4, PCl5 or POCl3 to give ArCHCl2 ArCOCl, ArCN and ArCO2H (where Ar = 2,6-dichlorophenyl), (2) the chlorinated mixture is oxidized (Cl2/H2O/FeCl3) to give mainly ArCO2H, (3) the oxidation product is reacted with SOCl2 to give mainly ArCOCl, and (4) the crude ArCOCl is reacted with NH3 to give ArCONH2 and the latter dehydrated with POCl3 to ArCN. |
