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CAS No. : | 221037-98-5 | MDL No. : | MFCD01319015 |
Formula : | C6H6BIO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | REEUXWXIMNEIIN-UHFFFAOYSA-N |
M.W : | 247.83 | Pubchem ID : | 2734362 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
In toluene;Reflux; | Into iodobenzeneboronic acid (186 g, 0.75 mol) and 700 (2 mL) were added to 1 L of a three-necked flask equipped with a reflux water separatorMl of toluene, heated to reflux water, when the system separated about 17.5-14.0 grams of water, and the system no longer continue to separate water,Stop the reaction. After cooling, the heptane is distilled to a non-flowing liquid to give crude tri-iodobenzene triol, which contains about 5-8percentbenzene. Can be directly into the next step reaction.Synthesis of aldehyde aldehyde phenylboronic acid:Under nitrogen protection, the above-obtained iodobenzeneboronic acid trimer was added to 500 ml of anhydrous tetrahydrofuranAfter the addition, the mixture was transferred to a 2 L three-necked flask and dimethylformamide (65.7 g, 0.90 mol) was added. Then cool the system to -75 ° C to -80 ° C, 609 ml (0.98 mol) of 1.6 M n-butyllithium hexane solution was slowly added dropwise, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; copper diacetate; In dichloromethane;Molecular sieve; under an oxygen balloon; | To a solution of 3-iodo-phenylboronic acid (991 mg, 4 mmol) and 1-benzofuran-6-ol (269 mg, 2 mmol) in dichloromethane (8 mL) was added copper acetate (363 mg, 2 mmol), pyridine (0.8 mL, 10 mmol) and 4A molecular sieves (300 mg). The reaction mixture was degassed and stirred under an oxygen balloon overnight. It was then filtered and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (0-10percent) in hexanes, to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; for 0.25h;Heating / reflux; Molecular sieves; | A mixture of <strong>[221037-98-5]3-iodophenylboronic acid</strong> (15 g) and 1, 3-diphenyl-1, 3-propanediol (15 g) in tetrahydrofuran (150 ML) was heated to reflux for 15 min in the presence of molecular sieves. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was crystallised from heptane-ethyl acetate (5: 1) to give the title compound (25.3 g) LCMS RT = 3.03 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; copper diacetate; In dichloromethane; at 20℃;4A molecular sieves; | To a stirred solution of Intemediate 1 (1.9 g, 8.5 mmol) in dichloromethane (20 mL) was added 3- iodophenylboronic acid (3.0 g, 12.1 mmol), copper(II) acetate (2.0 g, 11 mmol), pyridine (3.2 mL, 40 mmol), and 4A molecular sieves (~2.5 g). The resulting mixture was stirred under an oxygen balloon at room temperature overnight. The reaction mixuture was filtered, washed with dichloromethane, and concentrated. The greenish crude product was purified on a silica gel column, eluting with ethyl acetate (20-50percent) in hexanes to afford the desired product. LCMS for C 19Hl 9103: calc. 422, observed 423 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Example 1.52; Preparation of the intermediate (4-bromo-2-methyl-2H-pyrazoI-3-yI)-(3-iodo-phenyl)- amine.A 500-mL round bottom flask was charged with toluene (50 mL), copper(IT) acetate (0.62 g, 3.41 mmol), myristic acid (1.17 g, 5.11 mmol), and roe-iodophenylboronic acid (5.00 g, 20.18 mmol) then stirred at room temperature for five minutes. While mixing, 2,6-lutidine (1.99 mL, 17.04 mmol) was added and allowed to stir for an additional 10 minutes. 3-amino-4-bromo- 2-methyl pyrazole (3.00 g, 17.04 mmol) was added then reaction mixture stirred at room temperature overnight. Ethyl acetate was added, washed with ammonium hydroxide, water and brine. The ammonium salt formed, suspended in the organic layer, was removed by filtration. The filtrate was washed with water twice, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to yield a crude yellow oil, that was purified by column EPO <DP n="87"/>chromatography on silica gel (Biotage, hexanes/ethyl acetate, gradient elution) to afford (4- bromo-2-methyl-2H-pyrazol-3-yl)-(3-iodo-phenyl)-amine as a yellow solid. Yield: 3.25 g (51 percent). LCMS m/z (percent) = 378 (M+Eta 79Br, 100), 380 (M+Eta 81Br, 88). 1H NMR (400MHz, DMSO- d6): delta 8.15 (s, IH), 7.61 (s, IH), 7.09 (d, J=8.0 Hz, IH), 6.96 (dd, J=8.0, 8.0 Hz, IH), 6.90 (dd, J=I.8, 1.8 Hz, IH), 6.52 (dd, J=8.0, 1.6 Hz, IH), 3.63 (s, 3H). |
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