Hydrochloric Acid → 3-Chloro-5-nitrophenol

HRID 38550

反応式

HRID 38550 の反応式
[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

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 12064Benzene, 1,3-dichloro-5-nitro-HCID 14797Potassium HydroxideHCID 668498352-DI-Tert-Butylphosphino-2,4,6-Triisopropylbiphenyl

生成物 1

HCID 106758153-Chloro-5-nitrophenol収率 67.8%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒HCID 22728543Water ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6e688c6bb7214519b4f8e556437cacfe
出典データセット
uspto-grants-2013_09
特許番号
US08524722B2

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