Diethyl Ether → Benzoic acid 2-fluoro-pyridin-4-ylmethyl ester

HRID 426114

反応式

HRID 426114 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([F:9])[CH:4]=1.[C:10]([O-:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].CCOCC>CN(C=O)C>[F:9][C:5]1[CH:4]=[C:3]([CH2:2][O:18][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 517055Sodium BenzoateHCID 139851684-Bromomethyl-2-fluoropyridine

生成物 1

HCID 59184859Benzoic acid 2-fluoro-pyridin-4-ylmethyl ester収率 79.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The mixture of 4-Bromomethyl-2-fluoro-pyridine (35) (4.85 g, 25.5 mmol) and sodium benzoate (5.51 g, 38.25 mmol) in DMF (60 ml) was stirred at room temperature for 3 hr. Ether was then added and the mixture was washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4)) to afford 4.68 g (79%) of a colorless oil; 1H NMR (200 MHz, CDCl3) δ: 5.41 (2H, s), 7.11 (1H, m), 7.45-7.66 (3H, m), 8.08-8.12 (2H, m), 8.23 (1H, d, J=5.4 Hz); m/z (EI): 231 (M+).

後処理

  1. washthe mixture was washed with water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4))

出典と根拠

ORDレコード
ord-11432487aa5446ddbfa3e0ab506a8082
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

関連ノート

読み込み中…