2,2,2-Trifluoroethanol → 3-Bromo-5-(2,2,2-trifluoroethoxy)pyridine

HRID 24050ノート

反応式

HRID 24050 の反応式
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1>CN(C=O)C.O>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:15]=1

参加物

6

反応物 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

生成物 1

HCID 225703523-Bromo-5-(2,2,2-trifluoroethoxy)pyridine収率 46%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
70 °C

実験手順

To a slurry of sodium hydride (60% dispersion in mineral oil, 0.54 g, 14 mmol) in DMF (15 mL) was added commercially available 2,2,2-trifluoroethanol (0.97 mL, 14 mmol) at room temperature. After stirring for 15 minutes, a solution of 3,5-dibromopyridine (3.2 g, 14 mmol) in 5 mL of DMF was added dropwise. The reaction mixture was heated overnight at 70° C. After cooling to room temperature, the reaction was diluted with water and extracted with ethyl acetate. The extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (5% ethyl acetate/hexanes) to give the title compound (1.6 g, 46% yield) as clear oil. 1H NMR (CDCl3) δ 8.42 (d, 1H, J=1.7 Hz), 8.32 (d, 1H, J=2.5 Hz), 7.46 (m, 1H), 4.42 (m, 2H).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was chromatographed on silica (5% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-846bceea113f4a91acc8e987af3cd9ec
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

反応ノート

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