반응 #1929043

반응 방정식

Dibenzothiophene oxide

4-methoxybenzoic acid

Sodium iodide

Eaton's Reagent

→

title compound

수율 55.0%

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

수율 55.0%

용매

water

water

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도The reaction mixture was cooled back to 0° C.
3. 3
   기타quenched with the slow addition of water (800 mL)
4. 4
   여과The precipitate was filtered off
5. 5
   기타the layers separated
6. 6
   추출The aqueous layer was extracted with ethyl acetate (2×500 mL)
7. 7
   세척the combined organic layers were washed with water (500 mL)
8. 8
   기타The crude oil was recrystallized from acetone

실험 절차

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).

출처