反応 #1833228

反応方程式

3,5-Difluorobenzene-1,2-diol

thiophosgene

NaOH

→

title compound

収率 82.0%

4,6-Difluorobenzo[d][1,3]dioxole-2-thione

収率 82.0%

溶媒

chloroform

反応条件

後処理

1. 1
   その他the volatiles were removed by rotary evaporation
2. 2
   ろ過the residual solid was collected by filtration
3. 3
   洗浄washed with water
4. 4
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (30 mL)
5. 5
   洗浄washed with water (2×20 mL)
6. 6
   洗浄washed with saturated NaCl (1×10 mL)
7. 7
   乾燥dried (Na2SO4)
8. 8
   その他evaporated
9. 9
   その他The residue was purified by chromatography on silica with a 0-20% ethyl acetate-hexane gradient

実験手順

3,5-Difluorobenzene-1,2-diol (670 mg, 4.6 mmol) was stirred in dry chloroform (8 mL), treated with thiophosgene (580 mg, 5.0 mmol), cooled to 5-10° C., and treated dropwise with 10% NaOH solution (4.2 g, 11 mmol) over 45 min. After 30 min, the volatiles were removed by rotary evaporation and the residual solid was collected by filtration and washed with water. The solid was dissolved in ethyl acetate (30 mL), washed with water (2×20 mL), washed with saturated NaCl (1×10 mL), dried (Na2SO4), and evaporated. The residue was purified by chromatography on silica with a 0-20% ethyl acetate-hexane gradient to give the title compound (710 mg, 82%): 1H NMR (400 MHz, CDCl3) δ 6.95 (ddd, J=6.8, 2.3, 1.4 Hz, 1H), 6.89 (td, J=9.5, 2.3 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −109.99 (s), −127.93 (s); EIMS m/z 188.

出典