Reaktion #9072

Reaktionsgleichung

Na2CO3

4-bromobenzaldehyde

2-methoxybenzeneboronic acid

→

title compound

Ausbeute 92.0%

2′-methoxy-biphenyl-4-carboxaldehyde

Ausbeute 92.0%

Lösungsmittel

DME THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was flushed with argon
2. 2
   Temperaturmaintained under argon
3. 3
   TemperaturThe mixture was then cooled
4. 4
   workup.ADDITIONdiluted with EtOAc (25 mL) and water (25 mL)
5. 5
   WaschenThe aqueous layer was washed with EtOAc (2×10 mL)
6. 6
   Trocknenthe combined organic extracts dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigePurification of the resultant oil by column chromatography with silica gel (Hexanes/Et2O, 80:20)

Vorschrift

To a stirred degassed solution of 4-bromobenzaldehyde (218 mg, 1.18 mmol) and 2-methoxybenzeneboronic acid (188 mg, 1.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (1.6 mL) and Pd(PPh3)4 (63 mg, 0.055 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at 85° C. overnight. The mixture was then cooled and diluted with EtOAc (25 mL) and water (25 mL). The aqueous layer was washed with EtOAc (2×10 mL) and the combined organic extracts dried (Na2SO4), filtered and concentrated. Purification of the resultant oil by column chromatography with silica gel (Hexanes/Et2O, 80:20) afforded the title compound (230 mg, 92%) as a clear oil. 1H NMR (CDCl3) δ 3.84 (s, 3H), 7.01–7.09 (m, 2H), 7.33–7.39 (m, 2H), 7.71 (d, 2H, J=6 Hz), 7.93 (d, 2H, J=6 Hz), 10.05 (s, 1H).

Quelle