Reaction #66760

Reaction equation

H2O

[4-(methoxycarbonyl)phenyl]boronic acid

tert-butyl 4-bromo-3,5-diethoxybenzoate

K3PO4

→

4-tert-Butyl 4′-methyl 2,6-diethoxybiphenyl-4,4′-dicarboxylate

Solvents

DME

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered through celite pad
2. 2
   Concentrationthe filtrate was concentrated under reduced pressure
3. 3
   OtherThe residue was purified by silicage column chromatography (hexane/EtOAc)
4. 4
   Otherto give

Procedure

H2O (261 mg, 14.48 mmol) was added to a stirred mixture of PdCl2(dppf) (106 mg, 0.145 mmol), [4-(methoxycarbonyl)phenyl]boronic acid (626 mg, 3.48 mmol), tert-butyl 4-bromo-3,5-diethoxybenzoate (1.00 g, 2.90 mmol) and K3PO4 (1.23 g, 5.79 mmol) in DME (8 ml) and the mixture was stirred at 100° C. overnight. The reaction mixture was filtered through celite pad, the filtrate was concentrated under reduced pressure. The residue was purified by silicage column chromatography (hexane/EtOAc) to give intended compound as a colorless solid.

Source