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

HRID 18192

Reaction equation

HRID 18192 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-13b3e87c590b448f8662662dd0cb541e
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Linked notes

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