[1,1':4',1''-Terphenyl]-2,2''-dicarboxaldehyde synthesis
- Product Name:[1,1':4',1''-Terphenyl]-2,2''-dicarboxaldehyde
- CAS Number:1334652-46-8
- Molecular formula:C20H14O2
- Molecular Weight:286.32
99770-93-1
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Yield:1334652-46-8 67 %
Reaction Conditions:
Stage #1: benzene-1,4-diboronic acid bispinacol ester;ortho-bromobenzaldehydewith caesium carbonate in 1,2-dimethoxyethane;water;Inert atmosphere;
Stage #2: with tetrakis(triphenylphosphine) palladium(0) in 1,2-dimethoxyethane;water;Reflux;
Steps:
[1,1':4',1''-terphenyl]-2,2''-dicarbaldehyde (5).21
Compound 4 (0.410 g, 1.242 mmol), 2-bromobenzldehyde (0.662 g, 3.578 mmol) and Cs2CO3 (2.332 g, 7.157 mmol) were dissolved in a mixture of 1,2-dimethoxyethane (30 mL) and water (15 mL). The solution was purged with argon for 30 minutes, Pd(PPh3)4 (0.331 g, 0.286 mmol) was added and the reaction mixture was stirred at reflux for 16 hours. After evaporation of the solvents, the residue was dissolved in DCM (50 mL), filtered over celite and the filtrate was washed with water (3 x 50 mL). The organic phase was dried over MgSO4 and the solvent was evaporated in vacuum. The crude of reaction was purified by column chromatography. White solid (0.238, g η =67 %), Rf: 0.33, (silica gel, pentane/ethyl acetate 8/1). 1H-NMR (600 MHz, CDCl3), δ (ppm): 10.10 (s, 2H), 8.10 (dd, 3J = 7.8, 4J =1.1 Hz, 2H), 7.72 (td, 3J = 7.5, 4J =1.4 Hz, 2H), 7.58 (t, J = 7.6 Hz, 2H), 7.56-7.53 (overlapped peaks, 6H).
References:
Stroia, Ioan;Pop, Alexandra;Nan, Monica Irina;Bogdan, Elena;Terec, Anamaria;H?dade, Niculina D.;Grosu, Ion [Revue Roumaine de Chimie,2022,vol. 67,# 4-5,p. 233 - 239]
4612-26-4
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