Reaction #1929035

Reaction equation

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

3-hydroxyadamantane acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate sodium

water

→

title compound

Yield 99.0%

5-phenyl-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate

Yield 99.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe dichloromethane layer was separated
2. 2
   Washthe aqueous phase washed with dichloromethane (3×300 mL)
3. 3
   WashThe combined organic layers were washed with water (4×500 mL)
4. 4
   Concentrationconcentrated in vacuo and residual water
5. 5
   Otherremoved via azeotrope with acetonitrile (2×350 mL)

Procedure

5-phenyl-5H-dibenzo[b,d]thiophenium bromide (28.0 g, 82.04 mmol) and 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate-sodium salt (35.68 g, 83.7 mmol) were dissolved in dichloromethane (500 mL) and water (500 mL) and stirred at r.t. for 16 h. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×300 mL). The combined organic layers were washed with water (4×500 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×350 mL) to afford the title compound (54.00 g, 99%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.55 (d, J=8 Hz, 2H), 8.41 (d, J=8 Hz, 2H), 8.02 (dt, J=7.5, 0.5 Hz, 2H), 7.77-7.84 (m, 5H), 7.67 (t, J=7.5 Hz, 2H), 4.31 (t, J=6.5 Hz, 2H), 3.63 (s, 10H), 2.71 (tt, J=14, 6.5 Hz, 2H), 1.52-1.80 (m, 12H).

Source