Water → 4-Fluoro-3-(pyridin-2-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of commercially available 2-bromopyridine (250 mg; 1.58 mmol), 2-fluoro-5-formylphenylboronic acid (265 mg; 1.58 mmol), and Pd(PPh3)4 (91 mg; 0.08 mmol) in toluene (1 ml), EtOH (1 ml), and aq. 2 M Na2CO3 (1.5 ml) was heated to 80° C., under nitrogen, for 17 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded 4-fluoro-3-(pyridin-2-yl)benzaldehyde as a slightly yellow oil. LC-MS (conditions A): tR=0.51 min.; [M+H]+: 202.05 g/mol.

Provenance & Evidence