Hydrochloric Acid → HCID 90414931, compound

Temperature

5 °C

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.

1. stirringStirring
2. stirringstirred for 20 min more
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with dichloromethane (75 mL)
5. washThe combined organic phases were washed with saturated NaCl (30 mL)
6. dry with materialdried (Na2SO4)
7. customevaporated
8. customThe residue was purified by chromatography on silica with hexane

ORD record

ord-e15353b079c44587996abb631bd800b4

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2