[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](Cl)[CH:3]=1.[OH-:12].[K+].C(P(C(C)(C)C)C1(C(C)C)CC(C(C)C)=CC(C(C)C)=C1C1C=CC=CC=1)(C)(C)C.Cl>O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1
To a mixture of 1,3-dichloro-5-nitrobenzene (5.00 g, 26.0 mmol), potassium hydroxide (3.44 g, 52.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (539 mg, 0.52 mmol), and 2-(di-tert-butylphosphino)-2,4,6-triisopropylbiphenyl (885 mg, 2.08 mmol) was added a degassed mixture of dioxane (25 mL) and water (15 mL). The mixture was heated for 30 min to 80° C., then diluted with water/ethyl acetate and acidified with diluted hydrochloric acid. The mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1). The product was then triturated with petroleum ether/tert-butyl methyl ether and collected by suction filtration to yield 3.06 g (66%) of the title compound as yellowish crystals.
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