[1,1'-Biphenyl]-4-carboxaldehyde, 2',4',6'-trimethyl- synthesis

7synthesis methods

Product Name:[1,1'-Biphenyl]-4-carboxaldehyde, 2',4',6'-trimethyl-
CAS Number:106359-72-2
Molecular formula:C16H16O
Molecular Weight:224.3

5980-97-2 Synthesis

5980-97-2
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[1,1'-Biphenyl]-4-carboxaldehyde, 2',4',6'-trimethyl-

106359-72-2
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Yield:106359-72-2 80%

Reaction Conditions:

with bis-triphenylphosphine-palladium(II) chloride;sodium carbonate in Dimethyl ether;water;ethylene glycol at 100; for 5 h;Inert atmosphere;

Steps:

12.1 2',4',5'-Trimethyl-[1,1'-biphenyl]-4-carbaldehyde

4-bromobenzaldehyde 1a (10.0 g, 54.0 mmol),2.4.6-Trimethylphenylboronic acid 12a (10.2 g, 62.2 mmol),Bis(triphenylphosphine)palladium dichloride (1.90 g, 2.70 mmol)And sodium carbonate (17.2g, 162mmol)Soluble in 70mL dimethyl ether,In a mixed solution of ethylene glycol and water (V/V/V=4/2/1),The reaction was carried out at 100 °C for 5 hours under argon protection. The reaction mixture was diluted with ethyl acetate (200 mL).The organic phase was washed with saturated brine (100 mL×3), dried over anhydrous sodium sulfate and filtered.After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: System A).2′,4′,5′-Trimethyl-[1,1′-biphenyl]-4-carbaldehyde 12b (10.6 g, colorless liquid) was obtained in a yield of 80%.

References:

CN107759522,2018,A Location in patent:Paragraph 0475; 0479; 0480-0482