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CAS No. : | 128376-64-7 | MDL No. : | MFCD04972375 |
Formula : | C13H17BO3 | Boiling Point : | No data available |
Linear Structure Formula : | OHCC6H4B(OC(CH3)2C(CH3)2O) | InChI Key : | DMBMXJJGPXADPO-UHFFFAOYSA-N |
M.W : | 232.08 | Pubchem ID : | 2769536 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280 | UN#: | |
Hazard Statements: | H317 | Packing Group: | |
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 |
---|---|---|
513 mg | With sodium tetrahydroborate; at 20℃; for 5h; | To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75?77 °C) in88percent yield (513 mg). 1H-NMR (CD3OD-d4) delta ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) delta ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;11B-NMR (CDCl3) delta ppm 34.82. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Inert atmosphere; Reflux; | In a first step, 10 g (73.52 mmol) of 2,1,3-benzothiadiazole (1) was added to a 100 ml round-Suspended in 50 ml HBr solution (48percent),A solution of 2.8 ml (54.26 mmol) of bromine was added dropwise with vigorous stirring,After all the drops were added, the mixture was heated to 150 ° C and refluxed for 2 hours.After completion of the reaction, the mixture was cooled to room temperature,The reaction mixture was poured into 500 ml of water,The precipitated solid was filtered to give 10.4 g of crude product;The crude product contains a small amount of dibromo substituted product as well as the starting material.The crude product is directly put into the next step.Under nitrogen protection,To a 500 ml two-necked round bottom flask equipped with a condenser tube was added 8.556 g of crude product (assuming all <strong>[22034-13-5]4-bromo-2,1,3-benzothiadiazole</strong> (2), 40 mmol)10.208 g (44 mmol) of 4-formylphenylboronic acid pinacol ester,2.32 g (2.0 mmol) of tetrakis (triphenylphosphine) palladium and 200 ml of THF,Followed by the addition of 200 ml of an aqueous solution of potassium carbonate (11.06 g, 80 mmol), heated to reflux and stirred for 12 h.After completion of the reaction, the mixture was cooled to room temperature and the mixture was extracted three times with dichloromethane. The separated organic layer was dried over anhydrous sodium sulfate. The crude product obtained by distilling off the solvent under reduced pressure was treated with dichloromethane / petroleum ether (2: 1) as the eluent,Silica gel column chromatography afforded 8.2 g of pale yellow 4-formylphenyl-2,1,3-benzothiadiazole (3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 6h; | Pd(dppf)Cl2.CH2Cl2 (0.17 g, 0.0002 mole) was added to a stirred mixture of 4- bromothiazole (0.7 g, 0.004 mol), sodium carbonate ( 1.3 g, 0.012 mole) and 4-(4,4,5,5- tetramethyl-[l,3,2]dioxaborolan-2-yl)benzaldehyde (1.89 g, 0.008 mole) in a mixture of 1,4-dioxane and water (25 mL, 4: 1). The reaction mixture was heated to 80 °C and maintained for 6 hours, cooled to RT, diluted with H20 (10 mL), extracted with ethyl acetate (25 mL x 3). The organic extracts were combined, dried over anhydrous Na2S04 and concentrated under vacuum to obtain the crude 4-(thiazol-4-yl) benzaldehyde that was used as such for further reaction. |
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