Dimethylformamide → Methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate

HRID 1909330노트

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HRID 1909330 반응식
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:18]N(C=O)C.IC.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:15])([F:16])[F:17])=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 682955012-Methyl-3-nitro-5-(trifluoromethyl)benzoic acid

생성물 1

HCID 68295416Methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate수율 90%

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온도
60 °C

실험 절차

To a stirred solution of 2-methyl-3-nitro-5-(trifluoromethyl)benzoic acid (1 equiv.) in DMF (3 ml per 1 mmol), iodomethane (4 equiv.) and sodium carbonate (4 equiv.) were added. The resulting reaction mixture was stirred at 60° C. for 8 h. On completion, reaction mixture was filtered and the inorganic solid residue washed with ethyl acetate. The combined filtrate was concentrated under vacuum till dryness and the residue re-dissolved in ethyl acetate before washing with 5% sodium bicarbonate solution followed by 5M HCl solution. the organic layer was finally washed with brine, dried over sodium sulfate and concentrated to afford pure methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate (yield 90-95%).

후처리

  1. customThe resulting reaction mixture
  2. customOn completion, reaction mixture
  3. filtrationwas filtered
  4. washthe inorganic solid residue washed with ethyl acetate
  5. concentrationThe combined filtrate was concentrated under vacuum till dryness
  6. dissolutionthe residue re-dissolved in ethyl acetate
  7. washbefore washing with 5% sodium bicarbonate solution
  8. washthe organic layer was finally washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5bf94ad19221470385303ca5f9e067d1
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598167B1

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