Iodine → 4-Chloro-6-fluoro-2-(4-fluorophenyl)quinoline

HRID 638280

반응식

HRID 638280 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=2)[N:18]=[CH:17][CH:16]=1.II.[OH-].[Na+]>CCOCC.CCCCCC.O1CCCC1.O>[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=2)[N:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)[CH:16]=1

참가 물질

10

반응물 5

HCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 14798Sodium HydroxideHCID 27365864-Chloro-6-fluoroquinolineHCID 178418339Butyllithium

생성물 1

HCID 136038974-Chloro-6-fluoro-2-(4-fluorophenyl)quinoline수율 50.8%

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 4.37 g (25 mmol) of 1-bromo-4-fluorobenzene in 35 ml of ether cooled to -10° was added 15 ml of a 1.6M solution of butyl lithium in hexane in portions while maintaining the temperature below 0°. This mixture was stirred below 0° for 15 min. A solution of 3.63 g (20 mmol) of 4-chloro-6-fluoroquinoline in 20 ml of tetrahydrofuran was added while maintaining the temperature below 0°. The dark solution was stirred at room temperature for 20 min. To the reaction mixture was then added 5 ml of water and 5 g of iodine, and 10 ml of 3N sodium hydroxide. After 10 min of stirring the solid was collected to give 2.8 g of product, mp 130°-133°.

후처리

  1. temperaturewhile maintaining the temperature below 0°
  2. temperaturewhile maintaining the temperature below 0°
  3. stirringThe dark solution was stirred at room temperature for 20 min
  4. stirringAfter 10 min of stirring the solid
  5. customwas collected

출처 및 근거

ORD 기록
ord-5ff4f36850a84cac9655db6ac5e43a06
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560692

연결된 노트

불러오는 중…