تفاعل #46470

معادلة التفاعل

methyl iodide

sodium sulfite

sodium bicarbonate

7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-sulfonyl chloride

→

7-bromo-5-fluoro-3-(3-fluoro-benzyl)-2-methanesulfonyl-benzofuran

المردود 58.2%

المذيبات

water

water

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for three hours
2. 2
   درجة الحرارةThe mixture was heated to 50° C. for two hours
3. 3
   درجة الحرارةthen cooled to room temperature
4. 4
   استخلاصextracted twice with dichloromethane
5. 5
   تجفيفThe solution was dried over magnesium sulfate
6. 6
   أخرىpurified by preparative thin layer chromatography (1/4, ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر