Hydrogen Peroxide → Pyridine, 4-[4-fluoro-3-(trifluoromethyl)phenyl]-, 1-oxide

HRID 1246840ノート

反応式

HRID 1246840 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].[OH:18]O>ClCCl.O.C[Re](=O)(=O)=O.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N+:11]([O-:18])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:14]([F:17])([F:15])[F:16]

参加物

7

反応物 2

HCID 784Hydrogen PeroxideHCID 219067584-[4-Fluoro-3-(trifluoromethyl)phenyl]pyridine

生成物 1

HCID 21906801Pyridine, 4-[4-fluoro-3-(trifluoromethyl)phenyl]-, 1-oxide収率 94%

試薬・触媒・溶媒 4

HCID 178418406HCID 178418406、化合物触媒HCID 178477782HCID 178477782、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Then, 4-(4-fluoro-3-trifluoromethyl-phenyl)-pyridine-1-oxide 74 was prepared as follows. To a solution of compound 73 (2.49 g, 10.3 mmol) in dichloromethane (10 mL) was added methyltrioxorhenium(VII) (0.128 g, 0.515 mmol), followed by hydrogen peroxide in water (30%, 5.15 mL). The reaction mixture was stirred at room temperature for 16 hours. Manganese (IV) oxide (0.050 g) was added. The mixture was stirred for another 30 minutes. The organic layer was separated. The aqueous layer was extracted with more dichloromethane (2×10 mL). The combined organic phase was washed with brine (3×30 mL), dried over MgSO4 and filtered. After evaporating the solvent, the crude material was loaded to a silica gel column, eluting with 10% methanol in ethyl acetate to give a white solid 74 (2.51 g, 94%). 1H-NMR (CDCl3, 400 MHz) δ 7.35 (t, J=9.3 Hz, 1H), 7.49 (d, J=7.2 Hz, 2H), 7.74–7.82 (m, 2H), 8.30 (d, J=7.1 Hz, 2H); MS (DCI) m/z 258, 259 (M+H)+.

後処理

  1. customThen, 4-(4-fluoro-3-trifluoromethyl-phenyl)-pyridine-1-oxide 74 was prepared
  2. stirringThe mixture was stirred for another 30 minutes
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with more dichloromethane (2×10 mL)
  5. washThe combined organic phase was washed with brine (3×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customAfter evaporating the solvent
  9. washeluting with 10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-1df2e54e1efb43aa950e8aa4ac762e0b
出典データセット
uspto-grants-2006_10
特許番号
US07129247B2

反応ノート

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