Structure of 34907-53-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 34907-53-4 |
Formula : | C11H17BO2 |
M.W : | 192.06 |
SMILES Code : | CC1=C(B(OC)OC)C(C)=CC(C)=C1 |
MDL No. : | MFCD32068248 |
InChI Key : | NCEUIABFEQHUQB-UHFFFAOYSA-N |
Pubchem ID : | 15920607 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
Synthesis of bis(4-bromophenyl)(mesityl)borane To a stirred solution of 2-bromo-1,3,5-trimethylbenzene (5.9 g, 30.0 mmol) in dry Et2O (100 mL) is added dropwise n-butyllithium (1.60 M in hexane, 18.75 mL, 30.0 mmol) at -78 C. After stirring for 1 h, the mixture is added trimethyl borate (6.2 g, 60.0 mmol) and is stirred overnight at room temperature. The solvent of mixture is evaporated, and the residue is distilled under reduced pressure (200 torr) to afford clear liquid dimethyl mesitylboronate intermediate. To the solution of dimethyl mesitylboronate (1 g, 5.21 mmol) in dry THF (20 mL) is added (4-bromophenyl)magnesium bromide (0.5 M in THF, 32 mL, 16 mmol) at -78 C. under nitrogen atmosphere. The reaction mixture is allowed to stir at room temperature and poured into a large amount of water, and extracted with chloroform. The combined organic layer is washed with water, and dried over anhydrous Na2SO4. The residue is purified by column chromatography on silica gel (eluent: hexane/CHCl3=8:1, v/v) to afford a white solid (8.4 g, 63%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.8% | In a 3-neck 2 L flask, 34.1 g (64.5 mmol) of the intermediate (2) was dissolved in 645 mL of diethyl ether, and then cooled to -78 C. 57 mL (142 mmol) of n-butyllithium (n-BuLi, 2.5 M in Hexanes) was slowly added dropwise. After stirring at the same temperature for 1 hour, 13.6 g (70.9 mmol) of <strong>[34907-53-4]dimethyl mesitylboronate</strong> was slowly added dropwise. The mixture was stirred while slowly raising the temperature to room temperature. After the reaction was terminated using distilled water, the separated organic layer was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The reactant was solidified using methanol (MeOH) to form a beige solid compound (Intermediate (3))22.0 g (yield: 68.8%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Compound X was prepared according to the literature procedure {Org. Lett. 2006, 8, 2241). 2-bromo-N-(2-bromophenyl)-N-methylaniline (0.5 g, 1.5 mmol) was dissolved in 50 mL of diethyl ether and the solution cooled to -78 C. tert-Butyllithium (4.3 mL of 1.7 molar solution in pentane, 7.3 mmol) was added dropwise and the reaction mixture allowed to warm to 0 C and stirred for 30 minutes. Dimethylmesityldiboronate ester (0.37 g, 1.9 mmol) was dissolved in 10 mL of ether and added to reaction mixture dropwise. The reaction mixture was allowed to warm to room temperature, refluxed for 2 h, cooled, filtered through Celite with dichlormethane and concentrated. The crude product was chromatographed on silica gel with 9/1 hexane/ethyl acetate and further crystallized from hexane to give 0.13 g (55%) of the Compound X. |