Hydrochloric Acid → HCID 67398626, compound

Temperature

-78 °C

Under nitrogen atmosphere, n-butyllithium (1.6 mol/L-n-hexane, 18.8 mL) was added dropwise at −78° C. to a solution of n-hexane (11 mL) and tetrahydrofuran (30 mL). Then, a solution of 1-bromo-4-chloro-2-fluorobenzene (5.24 g) in n-hexane (15 mL) and tetrahydrofuran (15 mL) was added dropwise. The mixture was stirred at −78° C. for one hour, boric acid trimethyl ester (4.0 mL) in tetrahydrofuran (15 mL) was added dropwise. The mixture was raised to room temperature. After 2 hr, aqueous hydrochloric acid solution (3 mol/L, 120 mL) was added, and the mixture was extracted with diethyl ether (100 mL). The aqueous layer was extracted again with diethyl ether (100 mL), and the combined organic layers were dried over magnesium sulfate. The solvent was evaporated under reduced pressure, n-hexane was added to the residue, and the precipitated solid was collected by filtration to give the title compound (2.0 g) as a white solid.

1. temperatureThe mixture was raised to room temperature
2. waitAfter 2 hr
3. extractionthe mixture was extracted with diethyl ether (100 mL)
4. extractionThe aqueous layer was extracted again with diethyl ether (100 mL)
5. dry with materialthe combined organic layers were dried over magnesium sulfate
6. customThe solvent was evaporated under reduced pressure, n-hexane
7. additionwas added to the residue
8. filtrationthe precipitated solid was collected by filtration

ORD record

ord-83869f2deea647e795462a0bdc72d70d

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026370B2