反応 #8210

反応方程式

benzenesulfonyl chloride

ICl

CH2Cl2

5,7-difluoroindole

→

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

収率 87.0%

溶媒

toluene

NaOH

toluene

pyridine

反応条件

後処理

1. 1
   洗浄washed with brine, 1N HCl, 1N NaOH
2. 2
   乾燥dried (Na2SO4)
3. 3
   ろ過filtered
4. 4
   濃縮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
   その他The two phase reaction mixture
8. 8
   洗浄washed with brine, dried(Na2SO4)
9. 9
   ろ過filtered
10. 10
    濃縮concentrated
11. 11
    その他the residue is triturated with diethyl ether/petroleum ether
12. 12
    ろ過The resulting solid is filtered

実験手順

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%).

出典