Reaction #1833221

Reaction equation

3-Fluorobenzene-1,2-diol

thiophosgene

sodium hydroxide

→

title compound

Yield 77.0%

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

Yield 77.0%

Solvents

chloroform

Conditions

Workup

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

Procedure

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