Réaction #1929036

Équation de réaction

5-phenyl-5H-dibenzo[b,d]thiophenium bromide

triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

dichloromethane

→

title compound

Rendement 95.0%

5-phenyl-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

Rendement 95.0%

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   AutreThe dichloromethane layer was separated
2. 2
   Lavagethe aqueous phase washed with dichloromethane (3×500 mL)
3. 3
   LavageThe combined organic layers were washed with water (3×1 L)
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

5-phenyl-5H-dibenzo[b,d]thiophenium bromide (80.0 g, 234 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (78.5 g, 238 mmol) were dissolved in H2O (750 mL) and dichloromethane (750 mL) and stirred at r.t. for 18 h. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×500 mL). The combined organic layers were washed with water (3×1 L) and concentrated in vacuo to afford the title compound (109 g, 95%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.56 (dd, J=7.5, 1 Hz, 2H), 8.42 (d, J=8 Hz, 2H), 8.05 (dt, J=8 Hz, 1 Hz, 2H), 7.77-7.87 (m, 5H), 7.69 (dt, J=8, 1 Hz, 2H), 6.14-6.16 (m, 1H), 5.66-5.69 (m, 1H), 4.75 (dd, J=15, 15 Hz, 2H), 1.93-1.94 (m, 3H).

Source