반응 #46469

반응 방정식

7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran

2-bromo-4-fluoro-phenol

3-fluoro-cinnamaldehyde

Chlorosulfonic acid

pyridine

phosphorus pentachloride

→

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

용매

dichloromethane

dichloromethane

Water

반응 조건

후처리

1. 1
   온도then warmed to room temperature
2. 2
   workup.STIRRINGstirred for 16 hours
3. 3
   workup.STIRRINGthe reaction mixture was stirred for 24 hours
4. 4
   workup.STIRRINGthe reaction mixture was stirred for 30 minutes
5. 5
   기타The organic layer was separated
6. 6
   건조dried over magnesium sulfate
7. 7
   기타dried onto silica gel
8. 8
   기타layered over a pad of silica gel in a fritted funnel
9. 9
   세척The silica gel was eluted with ethyl acetate/hexanes (1/9)

실험 절차

7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran (0.97 gm, 3.0 mmol, prepared from 2-bromo-4-fluoro-phenol and 3-fluoro-cinnamaldehyde following the procedure of steps 1 and 2 of Example 8) was dissolved in dichloromethane (30 ml) and chilled to −15° C. Chlorosulfonic acid (0.26 ml, 3.9 mmol) in dichloromethane (2 ml) was added in portions, and the reaction mixture was stirred for 10 minutes then warmed to room temperature and stirred for 16 hours. To the resulting slurry was added pyridine (0.33 ml, 4.08 mmol) and phosphorus pentachloride (0.812 gm, 3.9 mmol) and the reaction mixture was stirred for 24 hours. Water was added and the reaction mixture was stirred for 30 minutes. The organic layer was separated, dried over magnesium sulfate, dried onto silica gel, and layered over a pad of silica gel in a fritted funnel. The silica gel was eluted with ethyl acetate/hexanes (1/9) to give 7-bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-sulfonyl chloride.

출처