Potassium Carbonate → HCID 68379851, compound

Dichlorobis(triphenylphosphine)palladium(II) (98%, 530 mg, 0.74 mmol) was added to a mixture of (5-fluoro-2-methoxyphenyl)boronic acid (10.0 g, 58.8 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (6.75 mL, 65.0 mmol) and potassium carbonate (16.3 g, 118 mmol) in tetrahydrofuran (100 mL) and water (30 mL), and the reaction mixture was stirred for 18 hours at room temperature. The aqueous layer was extracted with diethyl ether (100 mL), and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo, while keeping the bath temperature at <30° C. Pentane (200 mL) was added, the mixture was filtered, and the filtrate was concentrated under reduced pressure; the residue was subjected to silica gel chromatography (Eluent: pentane) to afford the product as a colorless oil. Yield: 9.08 g, 41.2 mmol, 70%. 1H NMR (400 MHz, CDCl3) δ 3.80 (s, 3H), 5.69-5.70 (m, 1H), 6.12-6.13 (m, 1H), 6.88 (dd, J=9.0, 4.5 Hz, 1H), 6.98 (br dd, J=8.8, 3.1 Hz, 1H), 7.05 (ddd, J=9.0, 7.8, 3.1 Hz, 1H).

1. extractionThe aqueous layer was extracted with diethyl ether (100 mL)
2. washthe combined organic layers were washed with saturated aqueous sodium chloride solution
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customat <30° C
7. additionPentane (200 mL) was added
8. filtrationthe mixture was filtered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-1e07f5cf68e34f009c24f219d8d8d9ed

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2