Réaction #1833231

Équation de réaction

NaHSO3

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

N-iodosuccinimide

NaCl

trifluoroacetic acid

→

title compound

Rendement 76.0%

4,6-Difluoro-5-iodobenzo[d][1,3]dioxole

Rendement 76.0%

Solvants

acetonitrile

ethyl acetate

Conditions de réaction

Traitement

1. 1
   LavageThe organic phase was washed with saturated NaCl (5 mL)
2. 2
   Séchagedried (Na2SO4)
3. 3
   Autreevaporated
4. 4
   AutreThe material was purified by chromatography on silica with a 0-5% ethyl acetate-hexane gradient

Mode opératoire

4,6-Difluorobenzo[d][1,3]dioxole (300 mg, 1.9 mmol) and N-iodosuccinimide (640 mg, 2.9 mmol) were combined in dry acetonitrile (5 mL), treated with trifluoroacetic acid (430 mg, 3.8 mmol) and stirred for 20 h. The mixture was stirred with a solution of NaHSO3 (100 mg in 2 mL water) and then shaken with ethyl acetate (30 mL) and saturated NaCl (5 mL). The organic phase was washed with saturated NaCl (5 mL), dried (Na2SO4) and evaporated. The material was purified by chromatography on silica with a 0-5% ethyl acetate-hexane gradient to give the title compound as a white solid (410 mg, 76%): mp 65-66° C. 1H NMR (400 MHz, CDCl3) δ 6.54 (dd, J=6.9, 1.6 Hz, 1H), 6.07 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −99.31, −117.98; EIMS m/z 284.

Source