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

Temperature

70 °C

A mixture of 3,5-dichlorophenylboronic acid (5 g, 26.2 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (5 g, 28.6 mmol), K2CO3 (7.24 g, 52.4 mmol) and Pd(PPh3)2Cl2 (368 mg) in THF (20 mL) and H2O (10 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether (50 mL) and H2O (50 mL). The aqueous layer was extracted with ether (50 mL) and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography over silica gel eluted with hexanes to afford 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (5.77 g; yield 85%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.42 (t, J=2.0 Hz, 2 H), 7.34 (d, J=2.0 Hz, 1 H), 6.05 (s, 1 H), 5.82 (s, 1 H) ppm.

1. temperatureThe mixture was cooled to rt
2. custompartitioned between ether (50 mL) and H2O (50 mL)
3. extractionThe aqueous layer was extracted with ether (50 mL)
4. dry with materialthe combined organic layers were dried over Na2SO4
5. customThe solvent was removed under reduced pressure
6. customthe crude product was purified by column chromatography over silica gel
7. washeluted with hexanes

ORD record

ord-97ee41b453814527b8ec0cb4a1995ca1

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156860B2