Cyclohexene oxide → HCID 67095951, compound

Temperature

-58 °C

To a solution of 1-bromo-3,4,5-trifluorobenzene (480 mg, 2.2 mmol) in diethyl ether (4.5 mL) was added drop wise at −76° C. under nitrogen butyl lithium (1.6 M in hexane, 1.31 mL, 2.1 mmol) keeping the temperature below −69° C. After 5 minutes cyclohexene oxide (216 uL, 2.1 mmol) was added dropwise keeping the temperature below −73° C. and then boron trifluoro etheroate (268 uL, 1.0 mmol) keeping the temperature below −66° C. The reaction was stirred for 30 minutes at −58° C. and then for 30 minutes at room temperature. Saturated aqueous ammonium chloride solution was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using heptane/ethyl acetate (7:3 v/v) as eluent to yield the title compound (221 mg, 43%) as an off-white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm)=6.83-6.91 (m, 2H), 3.57 (m, 1H), 2.37 (m, 1H), 2.10 (m, 1H), 1.75-1.86 (m, 3H), 1.26-1.56 (m, 5H).

1. customthe temperature below −69° C
2. customthe temperature below −73° C.
3. customthe temperature below −66° C
4. waitfor 30 minutes at room temperature
5. extractionthe reaction was extracted twice with diethyl ether
6. washThe combined organic layers were washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent was removed under reduced pressure
10. customThe residue was purified on silica gel

ORD record

ord-ca59d8dae3ed4fb6924335738e7fbd54

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923450B2