ChemicalBook CAS DataBase List methyl 3'-methylbiphenyl-4-carboxylate

methyl 3'-methylbiphenyl-4-carboxylate synthesis

9synthesis methods

Product Name:methyl 3'-methylbiphenyl-4-carboxylate
CAS Number:89900-94-7
Molecular formula:C15H14O2
Molecular Weight:226.27

17933-03-8
359 suppliers
$5.00/1g

99768-12-4 Synthesis

99768-12-4
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$10.00/1g

89900-94-7
24 suppliers
$45.00/50mg

Yield:89900-94-7 78%

Reaction Conditions:

Stage #1: 4-methoxycarbonylphenylboronic acidwith iodine;potassium carbonate in acetonitrile at 80; for 8 h;Inert atmosphere;Schlenk technique;Sealed tube;
Stage #2: m-tolylboronic acidwith palladium diacetate in acetonitrile at 80; for 14 h;Inert atmosphere;Schlenk technique;Sealed tube;Suzuki Coupling;

Steps:

General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8-12 h. The resulting solution was cooled to r.t., and thenarylboronic acid 1′ (0.75 mmol) and Pd(OAc)2 (0.025 mmol, 5.6 mg) were added, and the mixture stirred at 80 °C for 12-16 h. The resulting solution was cooled to r.t. and H2O (10mL) was added. The aq layer was extracted with EtOAc(3 × 5 mL). The combined organic phase was dried overanhydrous Na2SO4, filtered and concentrated by rotaryevaporation, and the residue was purified by columnchromatography on silica gel to provide the desired product3a-v. Data for three representative examples are provided

References:

Niu, Liting;Zhang, Hao;Yang, Haijun;Fu, Hua [Synlett,2014,vol. 25,# 7,art. no. 691,p. 995 - 1000] Location in patent:supporting information

1126-46-1 Synthesis