Reacción #1929046

Ecuación de reacción

2-phenylpropan-2-yl 2-bromoacetate

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

cesium carbonate

→

title compound

Rendimiento 97.5%

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

Rendimiento 97.5%

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with DCM (3×200 mL)
2. 2
   LavadoThe organic layers were washed with water (3×300 mL)
3. 3
   Concentraciónconcentrate
4. 4
   workup.ADDITIONpoured onto MTBE
5. 5
   FiltraciónThe precipitate was filtered
6. 6
   Otrodried

Procedimiento

2-phenylpropan-2-yl 2-bromoacetate (1.96 g, 7.63 mmol) was added to a solution of 5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium iodide (3.00 g, 6.94 mmol) and cesium carbonate (2.94 g, 9.02 mmol) in DMF (40 mL) at 0° C., warmed to r.t. and stirred overnight. The reaction mixture was diluted with water (200 mL) and washed with DCM (3×200 mL). The organic layers were washed with water (3×300 mL), concentrate and poured onto MTBE. The precipitate was filtered and dried to afford the title compound (3.80 g, 97%) as a white solid. 1H NMR (300 MHz, ((CD3)2SO) δ: 8.52 (d, J=7.5 Hz, 2H), 8.33 (d, J=7.5 Hz, 2H), 7.96 (t, J=7.2 Hz, 2H), 7.5 (d, J=7.9 Hz, 2H), 7.20-7.39 (m, 5H), 4.61 (s, 2H), 2.19 (s, 6H), 1.71 (s, 6H).

Fuente