تفاعل #682963

معادلة التفاعل

HCl

4-vinyl aniline

pyridine

2-(fluorosulfonyl)difluoroacetyl fluoride

→

solid

المردود 96.4%

1,1-difluoro-2-oxo-2-(4-vinylphenylamino) ethanesulfonyl fluoride

المردود 96.4%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 20 minutes
2. 2
   درجة الحرارةto warm to RT
3. 3
   workup.STIRRINGwas stirred for 4 hours at RT
4. 4
   أخرىreaction mixture
5. 5
   أخرىthe lower layer was separated
6. 6
   غسيلwashed with 1N HCl and brine
7. 7
   تجفيفThe solution was dried over MgSO4
8. 8
   ترشيحfiltrated
9. 9
   أخرىCH2Cl2 was removed by an evaporator

الإجراء التجريبي

A 100 ml flask was charged with CH2Cl2 (24 ml) under nitrogen stream and stirred for 10 min at 0° C. and then 2-(fluorosulfonyl)difluoroacetyl fluoride (6.60 g, 37.6 mmol, 1.5 eq.) was added. After 20 minutes, the CH2Cl2 (12 ml) solution of 4-vinyl aniline (2.86 g, 24.4 mmol, 1.0 eq.) and pyridine (1.93 g, 24.4 mmol, 1.0 eq.) was added dropwise to the mixture over 10 minutes. The mixture was allowed to warm to RT and was stirred for 4 hours at RT. 1N HCl was added to the final reaction mixture and the lower layer was separated and washed with 1N HCl and brine. The solution was dried over MgSO4, filtrated and then CH2Cl2 was removed by an evaporator. The target compound was obtained as a white solid (6.57 g) in 96% yield. 1H NMR (400 MHz, CDCl3); delta=5.28 (d, J=10.9 Hz, 1H), 5.74 (d, J=17.6 Hz, 1H), 6.68 (dd, J=10.9, 17.6 Hz, 1H), 7.43 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.7 Hz, 2H), 8.04 (brs, 1H). 19F-NMR (376 MHz, CDCl3, C6F6 as standard) delta=41.27 (t, J=4.6 Hz, 1F), −105.26 (d, J=4.2 Hz, 2F).

المصدر