Hydrochloric Acid → 3-Chloro-5-nitrophenol

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.

1. additionwas added
2. temperatureThe mixture was heated for 30 min to 80° C.
3. extractionThe mixture was extracted three times with ethyl acetate
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. customthe solvent was removed in vacuo
6. customThe crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)
7. customThe product was then triturated with petroleum ether/tert-butyl methyl ether
8. filtrationcollected by suction filtration

ORD record

ord-6e688c6bb7214519b4f8e556437cacfe

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524722B2