Reaktion #1980334

Reaktionsgleichung

methyl 3-bromo-4-methoxybenzoate

water

phenyl boronic acid

potassium carbonate

→

desired product

Ausbeute 95.0%

Methyl 6-methoxybiphenyl-3-carboxylate

Ausbeute 95.0%

Lösungsmittel

toluene

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigebubbled with argon for 6 min
2. 2
   workup.ADDITIONTetrakis(triphenylphosphine)palladium(0) (370 mg) was added
3. 3
   Sonstigebubbled with argon for another 2 min
4. 4
   TemperaturAfter cooling to RT
5. 5
   Sonstigethe two phases were separated
6. 6
   Extraktionthe aqueous layer was extracted with ether
7. 7
   Trocknendried with magnesium sulfate
8. 8
   Einengenconcentrated
9. 9
   SonstigePurification by MPLC (5% ethyl acetate in hexanes)

Vorschrift

To a solution of methyl 3-bromo-4-methoxybenzoate (13 g, 53 mmol) in toluene (500 mL), methanol (65 mL), and water (106 mL) was added phenyl boronic acid (7.8 g, 63.6 mmol) and potassium carbonate (14.6 g, 106 mmol) and bubbled with argon for 6 min. Tetrakis(triphenylphosphine)palladium(0) (370 mg) was added and bubbled with argon for another 2 min. The reaction mixture was then heated to 95° C. for 20 h with stirring. After cooling to RT, the two phases were separated and the aqueous layer was extracted with ether, dried with magnesium sulfate, and concentrated. Purification by MPLC (5% ethyl acetate in hexanes) gave 12.2 g of the desired product as an off white solid.

Quelle