Reaction #1929039

Reaction equation

1-ethylcyclopentyl 2-bromoacetate

5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide

cesium carbonate

→

title compound

Yield 94.1%

5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide

Yield 94.1%

Solvents

water

dichloromethane

dimethylformamide

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Extractionthe aqueous layer extracted with dichloromethane (4×150 mL)
3. 3
   ExtractionThe combined organic layers were extracted with water (2×300 mL)
4. 4
   Dryingdried (Na2SO4)
5. 5
   Concentrationconcentrated to the remaining DMF (−100 mL)
6. 6
   workup.ADDITIONThis non-viscous solution was slowly poured onto MTBE (700 mL) under vigorous stirring
7. 7
   FiltrationThe precipitate was filtered
8. 8
   Washwashed with MTBE (3×200 mL)
9. 9
   Otherthe residue dried in vacuo

Procedure

1-ethylcyclopentyl 2-bromoacetate (4.03 g, 17.1 mmol, 1.1 eq) was added dropwise to a solution of 5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide (6.00 g, 15.6 mmol) and cesium carbonate (10.15 g, 31.1 mmol, 2 eq) in dimethylformamide (150 mL) under N2 at 0° C. The solution was slowly warmed to r.t. and stirred for 16 h. The reaction mixture was diluted with water (400 mL) and dichloromethane (400 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (4×150 mL). The combined organic layers were extracted with water (2×300 mL), dried (Na2SO4) and concentrated to the remaining DMF (−100 mL). This non-viscous solution was slowly poured onto MTBE (700 mL) under vigorous stirring. The precipitate was filtered, washed with MTBE (3×200 mL) and the residue dried in vacuo to afford the title compound (7.92 g, 94%) as a white solid. 1H NMR (500 MHz, d-DMSO) δ: 8.51 (d, J=8 Hz, 2H), 8.32 (d, J=7.5 Hz, 2H), 7.96 (t, J=7.5 Hz, 2H), 7.75 (t, J=7.5 Hz, 2H), 7.31 (s, 2H), 4.51 (s, 2H), 2.21 (s, 6H), 1.93-2.03 (m, 2H), 1.92 (q, J=7 Hz, 2H), 1.49-1.69 (m, 6H), 0.79 (t, J=7 Hz, 3H).

Source