Dimethyl Sulfone → HCID 67997695, compound

5-Bromo-2-fluoro-pyridine (2.00 g) dissolved in tetrahydrofuran (20 mL) was added dropwise to a solution of sodium hexamethyldisilazide (2 mol/L in tetrahydrofuran, 28.5 mL) in tetrahydrofuran (20 mL) cooled to ca. −17° C. Dimethylsulfone (4.30 g) was added and stirring continued in the cooling bath for 1 h. The cooling bath was then removed and the solution was stirred at room temperature for one more h. Aqueous NH4Cl solution and brine were added and the resulting mixture was extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent was evaporated. The residue was treated with little ethyl acetate to precipitate the title compound. Yield: 1.73 g (63% of theory); LC (method 3): tR=2.01 min; Mass spectrum (ESI+): m/z=250/252 (Br) [M+H]+.

1. customThe cooling bath was then removed
2. stirringthe solution was stirred at room temperature for one more h
3. additionAqueous NH4Cl solution and brine were added
4. extractionthe resulting mixture was extracted with ethyl acetate
5. dry with materialThe combined extracts were dried (MgSO4)
6. customthe solvent was evaporated
7. additionThe residue was treated with little ethyl acetate
8. customto precipitate the title compound

ORD record

ord-9435f26960e94b9cb0360a012dcb825e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090605B2