反应 #8210

反应方程式

benzenesulfonyl chloride

ICl

CH2Cl2

5,7-difluoroindole

→

N-Benzenesulfonyl-3-iodo-5,7-difluoroindole

收率 87.0%

溶剂

toluene

NaOH

toluene

pyridine

反应条件

后处理

1. 1
   洗涤washed with brine, 1N HCl, 1N NaOH
2. 2
   干燥dried (Na2SO4)
3. 3
   过滤filtered
4. 4
   浓缩concentrated
5. 5
   workup.STIRRINGThe crude 3-iodo-5,7-difluoroindole is stirred in toluene (85 ml)
6. 6
   workup.STIRRINGthe resulting mixture is stirred 24 hours
7. 7
   其他The two phase reaction mixture
8. 8
   洗涤washed with brine, dried(Na2SO4)
9. 9
   过滤filtered
10. 10
    浓缩concentrated
11. 11
    其他the residue is triturated with diethyl ether/petroleum ether
12. 12
    过滤The resulting solid is filtered

实验过程

The 1.0 M ICl in CH2Cl2 (43 ml, 43 mmol) is added to a solution of 5,7-difluoroindole (6 g, 39 mmol) in 35 ml pyridine under N2 at 0° C. and the resulting mixture is stirred for 30 minutes. The reaction is diluted with toluene and washed with brine, 1N HCl, 1N NaOH, dried (Na2SO4), filtered and concentrated. The crude 3-iodo-5,7-difluoroindole is stirred in toluene (85 ml) and 5 N NaOH (70 ml), tetrabutylammonium bromide (1.25 g, 3.9 mmol), then benzenesulfonyl chloride (6.2 ml, 48 mmol) are added and the resulting mixture is stirred 24 hours. The two phase reaction mixture is diluted with toluene, washed with brine, dried(Na2SO4), filtered, concentrated and the residue is triturated with diethyl ether/petroleum ether. The resulting solid is filtered to give 14.2 g of N-Benzenesulfonyl-3-iodo-5,7-difluoroindole (87%).

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