反応 #1833231

反応方程式

NaHSO3

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

N-iodosuccinimide

NaCl

trifluoroacetic acid

→

title compound

収率 76.0%

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

収率 76.0%

溶媒

acetonitrile

ethyl acetate

反応条件

後処理

1. 1
   洗浄The organic phase was washed with saturated NaCl (5 mL)
2. 2
   乾燥dried (Na2SO4)
3. 3
   その他evaporated
4. 4
   その他The material was purified by chromatography on silica with a 0-5% ethyl acetate-hexane gradient

実験手順

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.

出典