Hydrochloric Acid → 3-(3-Bromophenyl)-4-(5-chloro-2-pyridyl)-2-butanol

To a solution of 3-(3-bromophenyl)-4-(5-chloro-2-pyridyl)-2-butanone (Step B, 6.7 g, 20 mmol) in 50 mL anhydrous THF at −78° C. was added lithium tri(sec-butyl)borohydride (1.0 M in THF, 30 mL, 30 mmol), and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., and was carefully added 2 M hydrochloric acid (50 mL), and the resulting mixture was partitioned between hexane (200 mL) and water (200 mL). The aqueous layer was separated and the organic layer extracted with 2 M hydrochloric acid (2×100 mL). The combined aqueous extracts were neutralized with 5 N aqueous sodium hydroxide (pH>12), and was extracted with EtOAc (2×200 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to afford the title compound.

1. temperatureThe reaction was cooled to 0° C.
2. customthe resulting mixture was partitioned between hexane (200 mL) and water (200 mL)
3. customThe aqueous layer was separated
4. extractionthe organic layer extracted with 2 M hydrochloric acid (2×100 mL)
5. extractionwas extracted with EtOAc (2×200 mL)
6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness

ORD record

ord-63851d96b8a64a2585eb3ea97d5c503f

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550489B2