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

HRID 426114

반응식

HRID 426114 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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))

출처 및 근거

ORD 기록
ord-11432487aa5446ddbfa3e0ab506a8082
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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