Dimethylformamide → 5-Bromo-2-(4-fluorophenoxy)pyridine

HRID 78008ノート

反応式

HRID 78008 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1.CN(C)C=O.[H-].[Na+]>O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:11][CH:12]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

生成物 1

HCID 574253025-Bromo-2-(4-fluorophenoxy)pyridine収率 75%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 4-fluorophenol (2.1 g, 19 mmol), 2,5-dibromopyridine (3.0 g, 13 mmol) and N,N-dimethylformamide (30 mL) was added sodium hydride (730 mg, 15 mmol, 50% in oil) at 0° C., which was stirred for 10 minutes at room temperature. The reaction mixture was then stirred for 5 hours at 110° C. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water twice, and then washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1) to obtain the title compound (2.6 g, 75%).

後処理

  1. stirringThe reaction mixture was then stirred for 5 hours at 110° C
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water twice
  5. washwashed with saturated aqueous sodium chloride
  6. concentrationwas concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1)

出典と根拠

ORDレコード
ord-3c03f2af31fe41bc840724fd878fd1bd
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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