反应详情

A mixture of commercially available 2-bromoisonicotinaldehyde (3.000 g; 16.12 mmol), phenylboronic acid (3.009 g; 24.19 mmol), and Pd(PPh3)4 (931 mg; 0.80 mmol) in toluene (40 ml) and aq. 2 M Na2CO3 (34 ml) was heated to reflux, under nitrogen, for 4 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 2-phenylisonicotinaldehyde as a yellow oil. LC-MS (conditions A): tR=0.39 min.; [M+H]+: 184.47 g/mol.

1. temperaturewas heated
2. temperatureto reflux, under nitrogen, for 4 h
3. extractionThe separated aq. layer was further extracted with AcOEt
4. washThe mixed organic layers were washed with brine
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure
8. customPurification by FC (heptane/AcOEt=7/3)