تفاعل #1833216

معادلة التفاعل

sodium iodide

sodium nitrite

2,2,6-Trifluorobenzo[d][1,3]dioxol-5-amine

hydrochloric acid

sodium bisulfite

→

title compound

المردود 51.0%

2,2,5-Trifluoro-6-iodobenzo[d][1,3]dioxole

المردود 51.0%

المذيبات

dichloromethane

water

water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGStirring
2. 2
   workup.STIRRINGstirred for 20 min more
3. 3
   أخرىThe phases were separated
4. 4
   استخلاصthe aqueous phase was extracted with dichloromethane (75 mL)
5. 5
   غسيلThe combined organic phases were washed with saturated NaCl (30 mL)
6. 6
   تجفيفdried (Na2SO4)
7. 7
   أخرىevaporated
8. 8
   أخرىThe residue was purified by chromatography on silica with hexane

الإجراء التجريبي

2,2,6-Trifluorobenzo[d][1,3]dioxol-5-amine (8.0 g, 42 mmol) was added to concentrated hydrochloric acid (conc. HCl; 200 mL), cooled to 5° C., vigorously stirred and treated dropwise with a solution of sodium nitrite (4.3 g, 63 mmol) in water (10 mL) over 10 min. Stirring was continued for 30 min at 5-10° C. and the mixture was poured cautiously into a solution of sodium iodide (19 g, 130 mmol) in water (200 mL), rapidly stirred with dichloromethane (100 mL). After 20 min the mixture was treated with 10% sodium bisulfite solution (NaHSO3; 20 mL) and stirred for 20 min more. The phases were separated and the aqueous phase was extracted with dichloromethane (75 mL). The combined organic phases were washed with saturated NaCl (30 mL), dried (Na2SO4) and evaporated. The residue was purified by chromatography on silica with hexane to give the title compound as a clear liquid (6 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=5.0 Hz, 1H), 6.90 (d, J=6.6 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −49.63 (s), −95.24 (s); EIMS m/z 302.

المصدر