تفاعل #1833221

معادلة التفاعل

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

المردود 77.0%

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

المردود 77.0%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىthe chloroform was removed under vacuum
2. 2
   أخرىthe solid formed
3. 3
   ترشيحwas collected by filtration
4. 4
   غسيلwashed with water
5. 5
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (100 mL)
6. 6
   غسيلthe solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. 7
   تجفيفdried (Na2SO4)
8. 8
   أخرىevaporated
9. 9
   أخرىThe crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

الإجراء التجريبي

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.

المصدر