Reaction #59102

Reaction equation

2-(2-fluoro-5-nitrophenyl)-2-methyloxirane

BF3

→

2-(2-fluoro-5-nitrophenyl) propanal

Solvents

ethyl ether

Conditions

Workup

1. 1
   OtherSolution was then quenched with water
2. 2
   Extractionextracted with ethyl ether
3. 3
   WashOrganics washed with brine
4. 4
   Dryingdried with sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   OtherCrude product was purified

Procedure

2-(2-fluoro-5-nitrophenyl)-2-methyloxirane (1 eq) was dissolved in ethyl ether (1 mL) under nitrogen. BF3-etherate (0.87 eq) was added dropwise at room temperature and after complete addition solution was allowed to stir for 1 h. Solution was then quenched with water, extracted with ethyl ether. Organics washed with brine, dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex: 15% EtOAc) on silica to afford 2-(2-fluoro-5-nitrophenyl) propanal.

Source