Reference of 19230-28-5, These common heterocyclic compound, 19230-28-5, name is 1,3-Dichloro-2-iodobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To toluene 3.0mL solution of tert-butyl 2-amino-4-phenethylbenzoate 0.10g were added 1,3-dichloro-2-iodobenzene 0.23g, cesium carbonate 0.22g, tris(dibenzylideneacetone)dipalladium(0) 3.0mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8.0mg at room temperature, and it was stirred at 110C for 24 hours. After the reaction mixture was cooled to room temperature, palladium acetate 1.5mg, tris(dibenzylideneacetone)dipalladium(0) 3.0mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8.0mg were added, and it was stirred at 110C for 20 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 2-(2,6-dichloroanilino)-4-phenethylbenzoate. Trifluoroacetic acid 10mL was added to the obtained tert-butyl 2-(2,6-dichloroanilino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 75-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(2,6-dichloroanilino)-4-phenethylbenzoic acid 9.4mg of white solid. 1H-NMR(DMSO-d6) delta value: 2.76(4H,m),6.04(1H,d,J=1.2Hz),6.66(1H,dd,J=8.1,1.2Hz),7 .08-7.24(5H,m),7.36(1H,t,J=8.2Hz),7.61(2H,d,J=8.3Hz),7.80(1 H,d,J=8.0Hz),9.52(1H,s),13.00(1H,s).
The synthetic route of 19230-28-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com