反应详情

A stirred mixture of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-bromomethyl-benzene (0.30 g), 3,5-difluoro-4-methoxy-phenylboronic acid (0.21 g) and potassium carbonate (0.31 g) in acetone (3 mL) and water (1 mL) under argon is cooled in an ice-bath. Then palladium dichloride (5 mg) is added and the cooling bath is removed. The reaction mixture is stirred at ambient temperature overnight. Then brine is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried over sodium sulfate, and the solvent is removed in vacuo. The residue is taken up in methanol (5 mL) aqueous potassium hydroxide solution (1 mL, 4 mol/L) is added. The solution is stirred at ambient temperature for 0.5 h and then neutralized with 1 M hydrochloric acid. The methanol is evaporated, and the residue is diluted with brine and extracted with ethyl acetate. The organic extracts are dried over sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->9:1).

1. temperatureis cooled in an ice-bath
2. customthe cooling bath is removed
3. additionThen brine is added
4. extractionthe resulting mixture is extracted with ethyl acetate
5. dry with materialThe combined extracts are dried over sodium sulfate
6. customthe solvent is removed in vacuo
7. additionis added
8. stirringThe solution is stirred at ambient temperature for 0.5 h
9. customThe methanol is evaporated
10. additionthe residue is diluted with brine
11. extractionextracted with ethyl acetate
12. dry with materialThe organic extracts are dried over sodium sulfate
13. customthe solvent is removed
14. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->9:1)