Hydrochloric Acid → HCID 59868825, compound

Temperature

-65 °C

2-Bromo-5-fluoro-pyridine (11 g, 62.5 mmol) was dissolved in diethyl ether at room temperature under a nitrogen atmosphere. The reaction mixture was cooled until the internal temperature was −66° C. Butyl lithium (2.5 M in hexanes, 26 mL, 65 mmol) was added dropwise over 0.5 h. The resulting reaction mixture was left at −65° C. for 1 h. N,N-Dimethylacetamide (6.5 mL, 70 mmol) was added over 10 min. and the reaction mixture was stirred at −65° C. for 2 h. 1M hydrochloric acid aq. (50 mL) was added and the mixture was warmed to room temperature. The pH was adjusted to 7 with additional hydrochloric acid. The aqueous phase was extracted with diethyl ether three times. The combined organic phases were washed with Brine, dried over sodium sulphate, and concentrated in vacuo. Purification by flash column chromatography (eluent heptane:diethyl ether gradient) yielded 4.6 g (34% yield) of the title compound.

1. temperatureThe reaction mixture was cooled until the internal temperature
2. customwas −66° C
3. customThe resulting reaction mixture
4. temperaturethe mixture was warmed to room temperature
5. extractionThe aqueous phase was extracted with diethyl ether three times
6. washThe combined organic phases were washed with Brine
7. dry with materialdried over sodium sulphate
8. concentrationconcentrated in vacuo
9. customPurification by flash column chromatography (eluent heptane:diethyl ether gradient)

ORD record

ord-9d3c2a584bec4b1db8d5b63f9e0745ac

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158785B2