反応 #1833221

反応方程式

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

収率 77.0%

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

収率 77.0%

溶媒

chloroform

反応条件

後処理

1. 1
   その他the chloroform was removed under vacuum
2. 2
   その他the solid formed
3. 3
   ろ過was collected by filtration
4. 4
   洗浄washed with water
5. 5
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (100 mL)
6. 6
   洗浄the solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. 7
   乾燥dried (Na2SO4)
8. 8
   その他evaporated
9. 9
   その他The crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

実験手順

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.

出典