Reacción #76331

Ecuación de reacción

3-bromo-4-fluorobenzaldehyde

morpholine

K2CO3

→

3-bromo-4-(4-morpholinyl)benzaldehyde

Rendimiento 58.2%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe slurry was refluxed for 18 h
2. 2
   OtroThe solvent was removed
3. 3
   Otrothe residue was partitioned between ethyl acetate and water
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated to a yellow oil
7. 7
   OtroPurification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane

Procedimiento

Ex-604A) To a pyridine (15 mL) solution of 3-bromo-4-fluorobenzaldehyde (1.0 g, 4.9 mmol) was added morpholine (0.5 mL, 5.7 mmol) and K2CO3 (0.69 g, 5.0 mmol), and the slurry was refluxed for 18 h. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4) and evaporated to a yellow oil. Purification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane gave 0.77 g (58%) of the desired 3-bromo-4-(4-morpholinyl)benzaldehyde product as an white solid. 1H NMR (CDCl3) δ3.18 (m, 4H), 3.90 (m, 4H), 7.10 (d, 1H), 7.78 (d, 1H), 8.07 (s, 1H), 9.83 (s, 1H).

Fuente