Reaction #162533

Reaction equation

1-(2-chloro-8-fluoroquinolin-3-yl)ethanol

→

1-(2-chloro-8-fluoroquinolin-3-yl)ethanone

Yield 72.0%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureto reflux for 2 h
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   workup.ADDITIONThe product was diluted with hexanes
6. 6
   Filtrationfiltered

Procedure

To a round-bottomed flask containing toluene (183 mL) was added 1-(2-chloro-8-fluoroquinolin-3-yl)ethanol (6.20 g, 27.5 mmol) and manganese dioxide (19.1 g, 220 mmol, 8 eq). The reaction was heated to reflux for 2 h, cooled to rt, filtered and concentrated. The product was diluted with hexanes and filtered to give as a white solid 1-(2-chloro-8-fluoroquinolin-3-yl)ethanone (4.43 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.40 (d, J=1.6 Hz, 1H), 7.71 (br d, J=8.2 Hz, 1H), 7.56 (td, J=7.8, 5.1 Hz, 1H), 7.54 (ddd, J=9.8, 7.8, 1.6 Hz, 1H). Mass Spectrum (ESI) m/e=223.9 (M+1).

Source