Reaction #1929036

Reaction equation

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

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

dichloromethane

→

title compound

Yield 95.0%

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

Yield 95.0%

Solvents

H2O

Conditions

Workup

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

Procedure

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