반응 #74505

반응 방정식

2-chloro-4-hydroxybenzonitrile

compound 86

(2S,3R,4R,5S,6R)-2-(4-Chloro-5-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-2-methoxyphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

triflic acid

NBS

→

title compound

수율 65.0%

5-Bromo-2-chloro-4-hydroxybenzonitrile

수율 65.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타to quenching with saturated sodium bisulfite
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   추출extracted with EtOAc
4. 4
   건조The organic layer was dried over anhydrous MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude residue was purified by column chromatography (5-40% EtOAc/hexanes)

실험 절차

To a solution of 2-chloro-4-hydroxybenzonitrile (compound 86, 10.0 g, 65.1 mmol) in acetonitrile (200 mL) was added triflic acid (10.0 mL, 71.6 mmol) and NBS (16.2 g, 91.2 mmol) at −30° C. The solution was allowed to warm up to room temperature and stirred overnight prior to quenching with saturated sodium bisulfite. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (5-40% EtOAc/hexanes) to yield title compound (9.80 g, 65%) as a white solid.

출처