تفاعل #1833228

معادلة التفاعل

3,5-Difluorobenzene-1,2-diol

thiophosgene

NaOH

→

title compound

المردود 82.0%

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

المردود 82.0%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىthe volatiles were removed by rotary evaporation
2. 2
   ترشيحthe residual solid was collected by filtration
3. 3
   غسيلwashed with water
4. 4
   workup.DISSOLUTIONThe solid was dissolved in ethyl acetate (30 mL)
5. 5
   غسيلwashed with water (2×20 mL)
6. 6
   غسيلwashed with saturated NaCl (1×10 mL)
7. 7
   تجفيفdried (Na2SO4)
8. 8
   أخرىevaporated
9. 9
   أخرىThe residue was purified by chromatography on silica with a 0-20% ethyl acetate-hexane gradient

الإجراء التجريبي

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.

المصدر