Ethyl Acetate → 2-(2,4-Difluoro-phenoxy)-5-nitro-isonicotinic acid methyl ester

HRID 457700

反応式

HRID 457700 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].[CH3:12][O:13][C:14](=[O:25])[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][N:18]=[C:17](Cl)[CH:16]=1.CCOC(C)=O>C1COCC1.O>[CH3:12][O:13][C:14](=[O:25])[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][N:18]=[C:17]([O:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:16]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1230512,4-DifluorophenolHCID 45480451Methyl 2-chloro-5-nitroisonicotinate

生成物 1

HCID 588201942-(2,4-Difluoro-phenoxy)-5-nitro-isonicotinic acid methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 2,4 difluorophenol (Aldrich Chemical Co.) (2.68 mL, 1.1 eq) in THF (60 mL) at 0° C. was added sodium hydride (60% in oil) (1.123 g, 1.1 eq), and the resulting mixture was stirred from 0° C. to room temperature over 1 hour. This solution was then added to compound (1A) (5.79 g, 26.7 mmol), and the resulting mixture was heated at reflux for 2 hours. TLC analysis confirmed that the reaction was complete, and the mixture was cooled to room temperature. EtOAc (300 mL) and water (100 mL) were added, the resulting mixture was partitioned, and the layers were separated. The organic layer was washed with water (3×100 mL) and brine (1×100 mL). Then the EtOAc layer was dried over magnesium sulfate, filtered, concentrated, and pumped to give the titled compound (1B) as an off-white powder (7.99 g, M+=310, Mp=90.2–91.4° C.)

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe resulting mixture was partitioned
  4. customthe layers were separated
  5. washThe organic layer was washed with water (3×100 mL) and brine (1×100 mL)
  6. dry with materialThen the EtOAc layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3fddf5fc3147439e9e59f4b03d968e9c
出典データセット
uspto-grants-2007_03
特許番号
US07189731B2

関連ノート

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