Reacción #1833221

Ecuación de reacción

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

Rendimiento 77.0%

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

Rendimiento 77.0%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe chloroform was removed under vacuum
2. 2
   Otrothe solid formed
3. 3
   Filtraciónwas collected by filtration
4. 4
   Lavadowashed with water
5. 5
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (100 mL)
6. 6
   Lavadothe solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. 7
   Secadodried (Na2SO4)
8. 8
   Otroevaporated
9. 9
   OtroThe crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

Procedimiento

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.

Fuente