Reacción #1929043

Ecuación de reacción

Dibenzothiophene oxide

4-methoxybenzoic acid

Sodium iodide

Eaton's Reagent

→

title compound

Rendimiento 55.0%

5-(5-carboxy-2-methoxyphenyl)-5H-dibenzo[b,d]thiophenium iodide

Rendimiento 55.0%

Disolventes

water

water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   TemperaturaThe reaction mixture was cooled back to 0° C.
3. 3
   Otroquenched with the slow addition of water (800 mL)
4. 4
   FiltraciónThe precipitate was filtered off
5. 5
   Otrothe layers separated
6. 6
   ExtracciónThe aqueous layer was extracted with ethyl acetate (2×500 mL)
7. 7
   Lavadothe combined organic layers were washed with water (500 mL)
8. 8
   OtroThe crude oil was recrystallized from acetone

Procedimiento

Dibenzothiophene oxide (57 g, 285 mmol) and 4-methoxybenzoic acid (47.7 g, 314 mmol, 1.1 eq) were suspended in dichloromethane (400 mL) and cooled to 0° C. where Eaton's Reagent (285 mL) was added dropwise. The solution was taken off ice and stirred overnight at r.t. The reaction mixture was cooled back to 0° C. and quenched with the slow addition of water (800 mL), followed by ethyl acetate (500 mL). The precipitate was filtered off and the layers separated. The aqueous layer was extracted with ethyl acetate (2×500 mL) and the combined organic layers were washed with water (500 mL). Sodium iodide (341.6 g, 2.28 mol, 4 eq) in water (500 mL) was slowly poured onto the combined aqueous layers. Additional water was slowly added until precipitation of a viscous oil stopped. The crude oil was recrystallized from acetone afford the title compound (72.0 g, 55%) as a white solid. 1H NMR (300 MHz, (d-DMSO) δ: 12.0-13.0 (brs, 1H), 8.54 (d, J=7.8 Hz, 2H), 8.35 (d, J=8.1 Hz, 2H), 8.21 (dd, J=8.7, 2.1 Hz, 1H), 7.99 (t, J=7.8 Hz, 2H), 7.79 (t, J=7.8 Hz, 2H), 7.51 (d, J=8.7 Hz, 1H), 7.44 (d, J=2.1 Hz, 1H), 4.08 (s, 3H).

Fuente