Cfc 113 → HCID 90413817, compound

Temperature

-75 °C

2,2,6,6-Tetramethylpiperidine (2.1 mL, 1.8 g, 12 mmol) was dissolved in dry tetrahydrofuran (15 mL), cooled to −75° C. and treated with n-butyllithium (n-BuLi, 2.5 M; 4.8 mL, 12 mmol), and the mixture was stirred for 30 min at −75° C. 5-Bromo-2,2-difluorobenzo[d][1,3]dioxole (2.0 g, 8.4 mmol) was added, and the mixture was stirred for 2 h at −75° C. 1,1,2-Trichloro-1,2,2-trifluoroethane (2.4 mL, 3.8 g, 20 mmol) was added and stirring was continued for 1.5 h. Saturated NH4Cl (10 mL) was added, and the mixture was shaken with diethyl ether (30 mL) and water (20 mL). The ether phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated under vacuum. The residue was purified by chromatography on silica with hexane and then repurified by reverse-phase HPLC using 75% acetonitrile to give the title compound as a clear liquid (640 mg, 28%): 1H NMR (400 MHz, CDCl3) δ 7.38 (dd, J=8.5, 5.1 Hz, 1H), 6.90 (dd, J=9.0, 4.7 Hz, 1H); EIMS m/z 332.

1. stirringthe mixture was stirred for 2 h at −75° C
2. stirringstirring
3. waitwas continued for 1.5 h
4. washThe ether phase was washed with saturated NaCl (10 mL)
5. dry with materialdried (Na2SO4)
6. customevaporated under vacuum
7. customThe residue was purified by chromatography on silica with hexane
8. customrepurified by reverse-phase

ORD record

ord-57d540e011964362ae5e4b8522152bf3

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2