반응 #1833221

반응 방정식

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

수율 77.0%

4-Fluorobenzo[d][1,3]dioxole-2-thione

수율 77.0%

용매

chloroform

반응 조건

후처리

1. 1
   기타the chloroform was removed under vacuum
2. 2
   기타the solid formed
3. 3
   여과was collected by filtration
4. 4
   세척washed with water
5. 5
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (100 mL)
6. 6
   세척the solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. 7
   건조dried (Na2SO4)
8. 8
   기타evaporated
9. 9
   기타The crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

실험 절차

3-Fluorobenzene-1,2-diol (5.0 g, 39 mmol) and thiophosgene (3.3 mL, 5.0 g, 42 mmol) were combined in chloroform (50 mL), cooled to 10° C. and treated dropwise over 30 min with sodium hydroxide (10% solution; 36 g, 90 mmol) with vigorous stirring. After stirring for 2 h at ambient temperature, the chloroform was removed under vacuum, and the solid formed was collected by filtration and washed with water. The solid was dissolved in ethyl acetate (100 mL), the solution was washed with water (30 mL) and saturated NaCl (30 mL), dried (Na2SO4) and evaporated. The crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane to give the title compound (1.5 g, 77%): mp 58-59° C.; 1H NMR (400 MHz, CDCl3) δ 7.28 (m, 1H), 7.12 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −131.32; EIMS m/z 170.

출처