Реакция #1833221

Уравнение реакции

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

Выход 77.0%

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

Выход 77.0%

Растворители

chloroform

Условия реакции

Обработка

1. 1
   Другоеthe chloroform was removed under vacuum
2. 2
   Другоеthe solid formed
3. 3
   Фильтрацияwas collected by filtration
4. 4
   Промывкаwashed with water
5. 5
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (100 mL)
6. 6
   Промывкаthe solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. 7
   Сушкаdried (Na2SO4)
8. 8
   Другоеevaporated
9. 9
   ДругоеThe crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

Методика

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.

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