Methyl iodide → 7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-2-methanesulfonyl-benzofuran

HRID 18192

반응식

HRID 18192 반응식
[Br:1][C:2]1[C:10]2[O:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]=2[CH:5]=[C:4]([F:23])[CH:3]=1.S([O-])([O-])=O.[Na+].[Na+].[C:30](=O)(O)[O-].[Na+].CI>C1COCC1.O>[Br:1][C:2]1[C:10]2[O:9][C:8]([S:11]([CH3:30])(=[O:13])=[O:12])=[C:7]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]=2[CH:5]=[C:4]([F:23])[CH:3]=1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 593449227-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-sulfonyl chloride

생성물 1

HCID 593449337-Bromo-5-fluoro-3-(3-fluoro-benzyl)-2-methanesulfonyl-benzofuran수율 58.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-sulfonyl chloride (0.63 gm, 1.5 mmol) was dissolved in THF (5 ml) and added dropwise to a mixture of sodium sulfite (0.504 gm, 4 mmol) and sodium bicarbonate (0.336 gm, 4 mmol) in water (12 ml). The mixture was refluxed for three hours, cooled to room temperature, and methyl iodide (0.75 ml, 12 mmol) was added. The mixture was heated to 50° C. for two hours then cooled to room temperature and stirred for 16 hours. The mixture was diluted with water and extracted twice with dichloromethane. The solution was dried over magnesium sulfate and purified by preparative thin layer chromatography (1/4, ethyl acetate/hexanes) to give 7-bromo-5-fluoro-3-(3-fluoro-benzyl)-2-methanesulfonyl-benzofuran (0.35 gm, 58% yield), (M+H)+ 402.

후처리

  1. temperatureThe mixture was refluxed for three hours
  2. temperatureThe mixture was heated to 50° C. for two hours
  3. temperaturethen cooled to room temperature
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe solution was dried over magnesium sulfate
  6. custompurified by preparative thin layer chromatography (1/4, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-13b3e87c590b448f8662662dd0cb541e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741326B2

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