N-Fluorobenzenesulfonimide → 4-Bromo-2-fluoromethyl-quinolin-8-ol

Temperature

-80 °C

A solution of lithium diisopropylamide (1.8 M in THF, 0.70 mL, 1.3 mmol) in anhydrous THF (1.0 mL) was added dropwise to a stirred solution of 4-bromo-2-methyl-quinolin-8-ol (100 mg, 0.420 mmol) in anhydrous THF (1.0 mL) at −80° C. After stirring for 1 h at −80° C., a solution of N-fluorobenzenesulfonimide (331 mg, 1.05 mmol) in anhydrous THF (1 mL) was added dropwise at −100° C. The reaction mixture was allowed to warm to −20° C. and was then quenched by the addition of concentrated aqueous NH4Cl (0.4 mL). The mixture was partitioned between DCM (30 mL) and water (5 mL). The aqueous layer was extracted with DCM (2×10 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM) to give the title compound. MS (m/z): 258.1 [M+H+].

1. temperatureto warm to −20° C.
2. customwas then quenched by the addition of concentrated aqueous NH4Cl (0.4 mL)
3. customThe mixture was partitioned between DCM (30 mL) and water (5 mL)
4. extractionThe aqueous layer was extracted with DCM (2×10 mL)
5. dry with materialthe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash chromatography on silica gel (elution with DCM)

ORD record

ord-7df531d32512405b8398b70e7e6b380b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410134B2