Sodium Hydroxide → HCID 123419834, compound

Temperature

78 °C

A RBF was charged with 3′-(difluoromethyl)-2,5′-difluoro-4-iodo-5-methoxy-1,1′-biphenyl (770 mg, 1.944 mmol), triisopropyl borate (0.580 mL, 2.53 mmol) and THF (9.719 mL). The flask was cooled to 78° C. for 10 min, then n-butyllithium solution, 2.5m in hexanes (1.011 mL, 2.53 mmol) was added drowpise over 1 min. The colorless solution turned green then yellow. After 30 min at 78° C., 2N aq. NaOH (10 mL) was added. The resulting biphasic mixture was stirred for 10 min, and partitioned between water (20 mL) and ether (50 mL). The layers were separated, and the ethereal layer was extracted with water (2×10 mL). The combined aqueous extracts were washed with ether (10 mL), and then were acidified with 6N aq. HCl (10 mL). The resulting aq. mixture was extracted with DCM (3×20 mL). The combined DCM layers were dried over sodium sulfate, filtered, and concentrated to give (3′-(difluoromethyl)-2,5′-difluoro-5-methoxy-[1,1′-biphenyl]-4-yl)boronic acid (111 mg, 0.353 mmol, 18.18% yield) as white solid. m/z (ESI) 315.0 (M+H)+.

1. custompartitioned between water (20 mL) and ether (50 mL)
2. customThe layers were separated
3. extractionthe ethereal layer was extracted with water (2×10 mL)
4. washThe combined aqueous extracts were washed with ether (10 mL)
5. extractionThe resulting aq. mixture was extracted with DCM (3×20 mL)
6. dry with materialThe combined DCM layers were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-ca0d8cb4495e42ad921e4d53be52b9b1

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212182B2