Tetrahydrofuran → 1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Temperature

75 °C

To a mixture of tetrahydrofuran (33 mL), ethylene glycol dimethyl ether (33 mL), and 4 N aqueous potassium hydroxide (33 mL) in a 200 mL Fisher-Porter sealed tube was added 3,5-dichlorophenylboronic acid (8.72 g, 45.7 mmol) and 2-bromo-3,3,3-trifluoro-propene (10.0 g, 57.2 mmol), followed by the addition of tetrakis(triphenylphosphine)-palladium(0) (264 mg, 0.229 mmol). The mixture was heated to 75° C. for 3′ h. Then the reaction mixture was partitioned between diethyl ether and water. The aqueous extract was washed with diethyl ether (2×20 mL). The organic extracts were combined, dried (MgSO4), and concentrated under reduced pressure to provide a residue. The residue was purified by silica gel chromatography and eluted with hexane to afford 4.421 g of the title compound as a clear oil.

1. customsealed tube
2. customThen the reaction mixture was partitioned between diethyl ether and water
3. extractionThe aqueous extract
4. washwas washed with diethyl ether (2×20 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customto provide a residue
8. customThe residue was purified by silica gel chromatography
9. washeluted with hexane

ORD record

ord-6f476d02a830407cbeccb9651586dba9

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073910B2