반응 #8210

반응 방정식

benzenesulfonyl chloride

ICl

CH2Cl2

5,7-difluoroindole

→

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

수율 87.0%

용매

toluene

NaOH

toluene

pyridine

반응 조건

후처리

1. 1
   세척washed with brine, 1N HCl, 1N NaOH
2. 2
   건조dried (Na2SO4)
3. 3
   여과filtered
4. 4
   농축concentrated
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
   기타The two phase reaction mixture
8. 8
   세척washed with brine, dried(Na2SO4)
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타the residue is triturated with diethyl ether/petroleum ether
12. 12
    여과The resulting solid is filtered

실험 절차

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%).

출처