[1,1'-Biphenyl]-4,4'-dicarboxylic acid, 3-hydroxy-, 4,4'-dimethyl ester synthesis
- Product Name:[1,1'-Biphenyl]-4,4'-dicarboxylic acid, 3-hydroxy-, 4,4'-dimethyl ester
- CAS Number:848155-29-3
- Molecular formula:C16H14O5
- Molecular Weight:286.28
22717-56-2
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Yield:848155-29-3 98%
Reaction Conditions:
with palladium diacetate;potassium carbonate;triphenylphosphine in 1,2-dimethoxyethane;water at 20; for 12 h;Inert atmosphere;
Steps:
2 Preparation of dimethyl 3-hydroxy-[1,1′-biphenyl]-4,4′-dicarboxylate (15):
To a solution of methyl 4-bromo-2-hydroxybenzoate (307 mg, 1.3 mmol) in (CH3OCH2)2/H2O (10 mL, 1:1) was added (4-(methoxycarbonyl)phenyl)boronic acid (287 mg, 1.6 mmol), Pd(OAc)2 (15 mg, 0.07 mmol), PPh3 (17 mg, 0.07 mmol) and K2CO3 (551 mg, 4 mmol). The mixture was stirred at room temperature under argon protection for 12 h. The solution was neutralized by 1N HCl, diluted with EtOAc, wash with H2O, brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel flash column chromatography (hexane/EtOAc=5:1) to afford compound 15 (363 mg, 98%). Yellow solid; 1H NMR (500 MHz, CDCl3) δ 10.82 (s, 1H), 8.12 (d, J=8.2 Hz, 2H), 7.92 (d, J=8.3 Hz, 1H), 7.68 (d, J=8.2 Hz, 2H), 7.24 (d, J=1.3 Hz, 1H), 7.15 (dd, J=8.3, 1.3 Hz, 1H), 3.98 (s, 3H), 3.95 (s, 3H).
References:
US2017/196940,2017,A1 Location in patent:Paragraph 0082
67-56-1
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