Cfc 113 → HCID 15767259, compound

Temperature

-78 °C

2,2-Difluorobenzo[d][1,3]dioxole (6.3 g, 39.8 mmol) was dissolved in tetrahydrofuran (66 mL) and cooled to −78° C. n-Butyllithium (2.5 M solution in hexanes; 16.74 mL, 41.8 mmol) was added dropwise, keeping the temperature below −70° C. The reaction mixture was then stirred at −78° C. for 1 h to ensure complete deprotonation. 1,2,2-Trifluorotrichloroethane (14.93 g, 80 mmol) was dissolved in tetrahydrofuran (33 mL) and cooled to −65° C. The lithiate was transferred via cannula into the solution of 1,2,2-trifluorotrichloroethane at a rate that allowed the temperature to remain between −60° C. and −65° C. during the addition. The reaction mixture was then allowed to warm to room temperature and partitioned between diethyl ether and water. The organic phase was concentrated and the product was flashed through 100 g of silica gel using hexane as a solvent to provide the title compound as a clear oil (5.74 g, 74.8%): 1H NMR (400 MHz, CDCl3) δ 7.08 (dd, J=8.2, 1.4 Hz, 1H), 7.03 (t, J=8.0 Hz, 1H), 6.97 (dd, J=7.9, 1.5 Hz, 1H); EIMS m/z 192.

1. additionwas added dropwise
2. customthe temperature below −70° C
3. temperaturecooled to −65° C
4. additionto remain between −60° C. and −65° C. during the addition
5. temperatureto warm to room temperature
6. custompartitioned between diethyl ether and water
7. concentrationThe organic phase was concentrated

ORD record

ord-f1135c5042a04b0ab2985274c266f783

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2