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

HRID 1854148ノート

反応式

HRID 1854148 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
60 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3237973811ac43b7bbe846d2ecaee213
出典データセット
uspto-grants-2015_02
特許番号
US08962620B2

反応ノート

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