Reaktion #1833231

Reaktionsgleichung

NaHSO3

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

N-iodosuccinimide

NaCl

trifluoroacetic acid

→

title compound

Ausbeute 76.0%

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

Ausbeute 76.0%

Lösungsmittel

acetonitrile

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic phase was washed with saturated NaCl (5 mL)
2. 2
   Trocknendried (Na2SO4)
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe material was purified by chromatography on silica with a 0-5% ethyl acetate-hexane gradient

Vorschrift

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.

Quelle