Réaction #1833221

Équation de réaction

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

Rendement 77.0%

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

Rendement 77.0%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   Autrethe chloroform was removed under vacuum
2. 2
   Autrethe solid formed
3. 3
   Filtrationwas collected by filtration
4. 4
   Lavagewashed with water
5. 5
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (100 mL)
6. 6
   Lavagethe solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. 7
   Séchagedried (Na2SO4)
8. 8
   Autreevaporated
9. 9
   AutreThe crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

Mode opératoire

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.

Source