反応 #2283479

反応方程式

2-Amino-2-(5-bromo-2-fluoro-phenyl)-3,3-difluoro-propan-1-ol

potassium hydrogencarbonate

2-nitrobenzenesulfonyl chloride

→

title compound

収率 37.2%

2-(5-Bromo-2-fluoro-phenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine

収率 37.2%

溶媒

acetonitrile

反応条件

後処理

1. 1
   workup.WAITAfter this period
2. 2
   温度the reaction mixture was cooled down
3. 3
   その他partitioned between saturated aqueous NaHCO3 solution and TBME
4. 4
   その他The layers were separated
5. 5
   洗浄washed with brine and TBME
6. 6
   乾燥The combined organic layers were dried over MgSO4.H2O
7. 7
   その他evaporated
8. 8
   その他The crude product was purified on a silica gel column
9. 9
   洗浄by eluting with hexane/dichloromethane 2/1→1/2

実験手順

2-Amino-2-(5-bromo-2-fluoro-phenyl)-3,3-difluoro-propan-1-ol (13.04 g, 45.9 mmol) [examples 42 step d)] was dissolved in 261 mL acetonitrile, 2-nitrobenzenesulfonyl chloride (22.38 g, 101 mmol) and potassium hydrogencarbonate (13.79 g, 138 mmol) were added. The mixture was heated to 80° C. and stirred over night. After this period, the reaction mixture was cooled down and partitioned between saturated aqueous NaHCO3 solution and TBME. The layers were separated, washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/dichloromethane 2/1→1/2 to give 7.71 g of the title compound as white crystals.

出典