Acetone → HCID 58243400, compound

Temperature

-78 °C

To a stirred solution of 2-bromo-5-fluoropyridine (1.0 g, 5.7 mmol) in diethyl ether (20 ml) under a nitrogen atmosphere at −78° C. was added sesBuLi (4.87 ml of a 1.4 M solution in heptanes, 6.8 mmol). The resulting dark orange solution was stirred for 30 minutes at −78° C. and acetone (0.84 ml, 11.4 mmol) was then added dropwise. After a further 1 hour the reaction temperature was raised to room temperature giving a clear yellow solution. This was quenched with water (2 ml), diluted with EtOAc (30 ml) and washed with water (2×20 ml), dried (MgSO4), filtered and concentrated. The residue was purified via silica FCC (using a gradient of eluents; 9:1 to 4:6 hexane/diethyl ether) to give the title product as colourless oil (395 mg, 45%).

1. temperatureAfter a further 1 hour the reaction temperature was raised to room temperature
2. customgiving a clear yellow solution
3. customThis was quenched with water (2 ml)
4. additiondiluted with EtOAc (30 ml)
5. washwashed with water (2×20 ml)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified via silica FCC (

ORD record

ord-0b2f38581c234a798205bce590cff063

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691804B2