Water → 1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

HRID 1019766노트

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HRID 1019766 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([OH:13])=[CH:6][C:5]=1[CH3:14].[CH3:15]I.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][CH3:15])=[CH:6][C:5]=1[CH3:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 235324-Chloro-5-methyl-2-nitrophenolHCID 24758Sodium hydride

생성물 1

HCID 158645661-Chloro-4-methoxy-2-methyl-5-nitrobenzene수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a suspension of sodium hydride (1.2 mmol) in DMF (6 mL), 4-chloro 3-methyl 6-nitrophenol (1.0 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minute then methyliodide was added at 0° C. and the mixture was stirred for 4 hours at room temperature. Water (60 mL) was added and the mixture extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica using 5-8% EtOAc in hexane to give the title compound (87%) as a solid.

후처리

  1. additionwas added at 0° C
  2. stirringthe mixture was stirred for 4 hours at room temperature
  3. extractionthe mixture extracted with EtOAc (3×50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica using 5-8% EtOAc in hexane

출처 및 근거

ORD 기록
ord-b4f56fc062134a22a5749301d7d96acf
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716287B2

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