Methyl iodide → 1,2,4-Trimethoxy-5-nitrobenzene

HRID 1179220

반응식

HRID 1179220 반응식
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([OH:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:12]([O-:14])=[O:13])[C:6]([O:11][CH3:15])=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2971214,5-Dimethoxy-2-nitrophenol

생성물 1

HCID 8224151,2,4-Trimethoxy-5-nitrobenzene수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
77.5 °C

실험 절차

A mixture of 4,5-dimethoxy-2-nitro-phenol (2.00 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol) and iodomethane (0.75 mL, 12 mmol) in DMF was placed in a sealed tube and heated at 75-80° C. for 20 h. The reaction was cooled and was filtered through Celite, washing with ethyl acetate. The filtrate was washed with water (the first wash was back-extracted with ethyl acetate), sodium bicarbonate and brine, was dried (sodium sulfate) and was evaporated. Purification by flash chromatography (SiO2) eluted with 1:1 ethyl acetate:hexanes provided 1,2,4-trimethoxy-5-nitro-benzene (1.20 g, 57% yield) as a yellow solid. 1H-NMR (CDCl3, 500 MHz) 7.53 (s, 1H), 6.50 (s, 1H), 3.92 (s, 3H), 3.91 (s, 3H), 3.84 (s, 3H) ppm; MS (FIA) 214.1 (M+H); HPLC (Method A) 3.253 min.

후처리

  1. customwas placed in a sealed tube
  2. temperatureThe reaction was cooled
  3. filtrationwas filtered through Celite
  4. washwashing with ethyl acetate
  5. washThe filtrate was washed with water (the
  6. washfirst wash
  7. extractionwas back-extracted with ethyl acetate), sodium bicarbonate and brine
  8. dry with materialwas dried (sodium sulfate)
  9. customwas evaporated
  10. customPurification by flash chromatography (SiO2)
  11. washeluted with 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-48df0215a847437ebf83cec48b249f75
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279469B2

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