反応 #74505

反応方程式

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

収率 65.0%

5-Bromo-2-chloro-4-hydroxybenzonitrile

収率 65.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他to quenching with saturated sodium bisulfite
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   抽出extracted with EtOAc
4. 4
   乾燥The organic layer was dried over anhydrous MgSO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The crude residue was purified by column chromatography (5-40% EtOAc/hexanes)

実験手順

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.

出典