Hydrochloric Acid → HCID 86727239, compound

Temperature

-78 °C

To a cold (−78° C.) solution of 4-fluorobenzo[b]thiophene (80.4 mg, 0.528 mmol) in anhydrous THF (1 mL) was added n-butyllithium (0.363 mL, 0.581 mmol) dropwise. The reaction mixture was stirred at −78° C. for 60 minutes. A solution of triisopropyl borate (0.146 mL, 0.634 mmol) was added. The reaction mixture was stirred at −78° C. for 30 minutes and was then allowed to warm to room temperature over a 2 hour period. TLC showed completion of reaction. 1N HCl (100 mL) and DCM (50 mL) were added to the reaction mixture. The aqueous and organic layers were separated. The aqueous layer was concentrated to 50 mL, yielding a solid precipitate that was filtered and dried to give the title compound as off-white, needle-shaped crystals. The product was used without further purification.

1. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
2. temperatureto warm to room temperature over a 2 hour period
3. customcompletion of reaction
4. customThe aqueous and organic layers were separated
5. concentrationThe aqueous layer was concentrated to 50 mL
6. customyielding a solid precipitate that
7. filtrationwas filtered
8. customdried

ORD record

ord-164e0292e44948e3be73df1b8946ecb2

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056873B2