Pyrrolidine → 5-Fluoro-2-(pyrrolidin-1-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a mixture of pyrrolidine (328 mg, 3.05 mmol), 2-bromo-4-fluorobenzaldehyde (619 mg, 3.05 mmol) in toluene (10 ml) was added Cs2CO3 (2.48g, 7.62 mmol), BINAP (95 mg ) and palladium(II) acetate (35 mg) was added. The mixture was purged with Ar for 5 min, then heated at 95 oC for 4 hrs. After cooled to RT, EtOAc (30 mL) was added. The organic layer was washed with water (3 x 30 mL), brine (30 mL), dried over MgSO4, filetred and concentrated. The residue was purified via combiflush (0 - 20% EtOAc/Hexane; 40 g column) to give the desired product as a clear reddish liquid. LCMS and H-NMR look good. 290 mg Conclusion: reaction progressed to give desired product in 49% yield.

Provenance & Evidence