Réaction #2275718

Équation de réaction

methyl 4-bromo-2-methoxybenzoate

4-chlorophenyl boronic acid

K3PO4

→

desired compound

Rendement 78.0%

4′-chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester

Rendement 78.0%

Solvants

1,4-dioxane

MeOH

Conditions de réaction

Traitement

1. 1
   TempératureAfter this time, the reaction is cooled to room temperature
2. 2
   Filtrationfiltered through Celite™
3. 3
   AutreThe solids that form are collected
4. 4
   Lavagewashed with additional MeOH before the filtrate
5. 5
   Concentrationis concentrated under reduced pressure
6. 6
   AutreThe crude material is purified over silica (hexanes:EtOAc; 6:1 to 4:1)

Mode opératoire

To a degassed solution of methyl 4-bromo-2-methoxybenzoate (0.70 g, 2.86 mmol) in 1,4-dioxane (10 mL) and MeOH (2.5 mL) is added 4-chlorophenyl boronic acid (0.536 g, 3.43 mmol), Pd(dppf)Cl2 (0.233 g, 0.286 mmol) and K3PO4 (0.728 g, 3.43 mmol). The resulting suspension is heated to 80° C. and stirred for 3 hours. After this time, the reaction is cooled to room temperature and filtered through Celite™. The solids that form are collected and washed with additional MeOH before the filtrate is concentrated under reduced pressure. The crude material is purified over silica (hexanes:EtOAc; 6:1 to 4:1) to provide 0.615 g (78% yield) of the desired compound as orange crystals. 1H NMR (400 MHz, CDCl3) δ ppm 7.89 (1H, d, J=8.0 Hz), 7.52-7.56 (2H, m), 7.44 (2H, d, J=8.7 Hz), 7.17 (1H, d, J=8.0 Hz), 7.12 (1H, d, J=1.6 Hz), 3.99 (3H, s), 3.92 (3H, s). HPLC-MS: m/z 277 [M+H]+.

Source