Reaktion #1833221

Reaktionsgleichung

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

Ausbeute 77.0%

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

Ausbeute 77.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle