Iodine → HCID 90413796, compound

Temperature

-40 °C

Sec-Butyllithium (1.4 M in cyclohexane; 6.1 mL, 8.5 mmol) was added to dry tetrahydrofuran (15 mL) which had been pre-cooled to −40° C. The solution was cooled to −75° C., treated with 2,2,5-trifluorobenzo[d][1,3]dioxole (1.5 g, 8.5 mmol) and stirred at this temperature for 90 min. This solution was rapidly transferred via cannula into a stirred solution of iodine (2.8 g, 11 mmol) in tetrahydrofuran (25 mL), and the mixture was cooled to −75° C. The mixture was stirred for 1 h during which time the temperature rose to −20° C. The reaction was quenched by addition of saturated NH4Cl (10 mL) and then combined with 10% NaHSO3 (15 mL) and ethyl acetate (30 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated. The material was purified by flash chromatography with hexane to give the title compound as a clear liquid (1.5 g, 58%): 1H NMR (400 MHz, CDCl3) δ 6.97 (dd, J=8.8, 4.0 Hz, 1H), 6.81 (dd, J=11.7, 5.4 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −49.06, −103.15; EIMS m/z 302.

1. temperatureThe solution was cooled to −75° C.
2. temperaturethe mixture was cooled to −75° C
3. stirringThe mixture was stirred for 1 h during which time the temperature
4. customrose to −20° C
5. customThe reaction was quenched by addition of saturated NH4Cl (10 mL)
6. washThe organic phase was washed with saturated NaCl (10 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated
9. customThe material was purified by flash chromatography with hexane

ORD record

ord-813bed3d1064405bb013c45de9296ed1

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2