Ethyl Acetate → 2-Fluoro-N,N-dimethyl-4-(pyridin-4-yl)aniline

HRID 240226ノート

反応式

HRID 240226 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]([N:6]([CH3:8])[CH3:7])=[C:4]([F:11])[CH:3]=1.C(B(CC)[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)C.[OH-].[K+].C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Cl-].[Na+].O>[F:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:5]=1[N:6]([CH3:8])[CH3:7]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 133188714-(Diethylboranyl)pyridineHCID 404253644-bromo-2-fluoro-N,N-dimethylaniline

生成物 1

HCID 672021852-Fluoro-N,N-dimethyl-4-(pyridin-4-yl)aniline収率 46.2%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

4-Bromo-2-fluoro-N,N-dimethyl aniline (2.83 g, 13 mmols), tetrakis triphenyl palladium (0) (0.508 g, 0.4 mmols), diethyl (4-pyridyl borane) (1.3 g, 9 mmols), potassium hydroxide (2.81 g, 50 mmols) and tetrabutylammonium bromide (1.42 g, 4 mmols) were combined in tetrahydrofuran (50 ml). The resulting mixture was heated at reflux for 18 hrs under nitrogen then cooled to ambient temperature. Ethyl acetate (100 ml) and brine (50 ml) were added and the organic solution was separated. This was dried over magnesium sulfate filtered and evaporated to yield a yellow solid. The product was purified by column chromatography on silica eluted with ethyl acetate:hexanes 50:50 to give 0.9 g of 2-Fluoro-N,N-dimethyl-4-(pyridin-4-yl)aniline (XII) in a 44% yield as a pale yellow solid.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 hrs under nitrogen
  3. customthe organic solution was separated
  4. dry with materialThis was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a yellow solid
  8. customThe product was purified by column chromatography on silica
  9. washeluted with ethyl acetate:hexanes 50:50

出典と根拠

ORDレコード
ord-679ebbcbb9de42268d302d621ffbe7de
出典データセット
uspto-grants-2014_02
特許番号
US08647827B2

反応ノート

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