تفاعل #308925

معادلة التفاعل

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

2-nitrobenzenesulfonyl chloride

potassium hydrogencarbonate

→

title compound

المردود 37.2%

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

المردود 37.2%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter this period
2. 2
   درجة الحرارةthe reaction mixture was cooled down
3. 3
   أخرىpartitioned between saturated aqueous NaHCO3 solution and TBME
4. 4
   أخرىThe layers were separated
5. 5
   غسيلwashed with brine and TBME
6. 6
   تجفيفThe combined organic layers were dried over MgSO4.H2O
7. 7
   أخرىevaporated
8. 8
   أخرىThe crude product was purified on a silica gel column
9. 9
   غسيلby eluting with hexane/dichloromethane 2/1->1/2

الإجراء التجريبي

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.

المصدر