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

HRID 601012

反応式

HRID 601012 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 8224151,2,4-Trimethoxy-5-nitrobenzene収率 57%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
77.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d0cb3f73ea544a2e9dd67cb12c01bfa6
出典データセット
uspto-grants-2011_03
特許番号
US07902239B2

関連ノート

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