Dimethylformamide → 2-(4-Bromo-benzyloxy)-3-fluoro-pyridine

HRID 78147

反応式

HRID 78147 の反応式
CN(C)C=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.[H-].[Na+].Cl[C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][N:19]=1>O>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 27827912-Chloro-3-fluoropyridine

生成物 1

HCID 592552352-(4-Bromo-benzyloxy)-3-fluoro-pyridine収率 98%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an N,N-dimethylformamide (15 mL) solution of (4-bromo-phenyl)-methanol (1.56 g, 8.34 mmol) was added sodium hydride (401 mg, 8.35 mmol, 50% in oil), which was stirred for 5 minutes at room temperature. Then, an N,N-dimethylformamide (5 mL) solution of 2-chloro-3-fluoropyridine (967 mg, 7.35 mmol) was added to this mixture, which was stirred for 1 hour and 10 minutes at room temperature. Water was to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane: ethyl acetate=2:1) to obtain the title compound (2.03 g, 98%).

後処理

  1. stirringwas stirred for 1 hour and 10 minutes at room temperature
  2. customwas to the reaction mixture at room temperature
  3. extractionwhich was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (heptane: ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-461f222fd091484488f6bd2d97d92091
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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