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CAS No. : | 118062-05-8 | MDL No. : | MFCD01318183 |
Formula : | C9H13BO5 | Boiling Point : | - |
Linear Structure Formula : | C6H2(OCH3)3B(OH)2 | InChI Key : | LDQLSQRFSNMANA-UHFFFAOYSA-N |
M.W : | 212.01 | Pubchem ID : | 2773582 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; | (The following reaction is done in an N2 atmosphere.) To a solution of 2,3,4-Trimethoxyphenylboronic acid (32) (1.40g, 6.60mmol) in toluene (15.0mL) is added EtOH (2.0mL), Pd(PPh3)4 (208mg, 0.18mmol) and Na2CO3·10H2O (4.81g, 16.80mmol) in water (5.2mL). The resulting mixture is carefully degassed (5 times alternating vacuum and flushing with N2). A solution of Methyl-3-bromobenzoate (9) (1.29g, 6.00mmol) in toluene (9.0mL) is added by syringe, the resulting mixture is again carefully degassed and stirred overnight at 100C. Partition the mixture between brine/EtOAc (1+1), separate layers, extract the aqu. layer with EtOAc (3x), wash the combined organic layer with brine, dry with Na2SO4 and remove solvent. Purify crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+5) to obtain 2',3',4'-Trimethoxy-biphenyl-3-carboxylic acid methyl ester (33) as a yellowish oil (1.07g, 58%). 1H NMR (400MHz, CDCl3): 3.66 (s, 3 H); 3.89 (s, 3 H); 3.92 (s, 6 H); 6.74 (d, 1 H, J= 8.6Hz); 7.03 (d, 1 H, J = 8.6Hz); 7.44 (t, 1 H, J = 7.8Hz); 7.70 (d, 1 H, J = 7.6Hz); 7.97 (d, 1 H, J = 7.8Hz); 8.15 (br.s 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 6h;Inert atmosphere; | General procedure: A 1,4-dioxane solution (3?mL) of 1, arylboronic acid (1.2?equiv), aqueous K2CO3 (2.0?M, 1.0?mL) and Pd(PPh3)4 (3?mol?percent) was heated at 80?°C for 6?h under argon atmosphere. After cooling to 20?°C, H2O was added and the reaction mixture was extracted with CH2Cl2 (3×25?mL). The organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, heptane/EtOAc).#10; |
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