Reaktion #1929049

Reaktionsgleichung

5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide

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

water

→

title compound

Ausbeute 80.0%

5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

Ausbeute 80.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe dichloromethane layer was separated
2. 2
   Waschenthe aqueous phase washed with dichloromethane (3×100 mL)
3. 3
   WaschenThe combined organic layers were washed with water (4×100 mL)
4. 4
   Einengenconcentrated in vacuo and residual water
5. 5
   Sonstigeremoved via azeotrope with acetonitrile (2×100 mL)

Vorschrift

5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium bromide (7.00 g, 12.5 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (4.21 g, 12.7 mmol) were dissolved in dichloromethane (100 mL) and water (100 mL) and stirred at room temperature overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×100 mL). The combined organic layers were washed with water (4×100 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×100 mL) to afford the title compound (7.07 g, 80%) as a white solid. 1H NMR (300 MHz, (CD3)2CO) δ: 8.53 (d, J=7.8 Hz, 2H), 8.37 (d, J=7.8 Hz, 2H), 8.03 (t, J=7.8 Hz, 2H), 7.82 (t, J=7.8 Hz, 2H), 7.52 (s, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.32 (t, J=8.1 Hz, 2H), 7.26 (t, J=8.1 Hz, 1H), 6.12-6.19 (m, 1H), 5.68-5.71 (m, 1H), 4.76 (t, J=15.6 Hz, 2H), 4.66 (s, 2H), 2.28 (s, 6H), 1.94 (s, 3H), 1.77 (s, 6H).

Quelle