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CAS No. : | 371193-08-7 | MDL No. : | MFCD14636522 |
Formula : | C25H35BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 378.36 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
72% | General procedure: To a solution of corresponding arylbromide (4-6; 1.0 equiv.) in dry THF (10mL) at-78C was added n-butyllithium (in hexane, 1.6M; 3.0 equiv.) under N2 atmosphere and stirred at this temperature for 1hr. B(OMe)3 (3.0 equiv.) was then added slowly at-78C and the resulting solution was stirred for another 1.5h without cooling bath before the addition of 6M HCl(aq) (10mL). The acidified solution was continuously stirred at room temperature for overnight and then was extracted with ethyl acetate (20mL×3). The combined organic layer was collected and dried over MgSO4(S). After removing the solvent, the crude product was purified through column chromatography on silica with properly combined ethyl acetate and hexane as the eluent to give final purified product and was used for the next step of synthesis directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.9% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene at 50℃; for 114h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium carbonate In tetrahydrofuran; water; toluene at 105℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrabutylammomium bromide; potassium carbonate In toluene at 80℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In water; toluene for 24h; Reflux; Inert atmosphere; | 1 Synthesis of compound A (scheme 1)To a mixture of 2,7-dibromofluorenone (1.8 g,5.3mmol), prepared as above, 9,9-dihexyfluorene-2-boronic acid (5.0 g, 13.2 mmol), and tetrakis(triphenylphosphine)palladium (0.123 g, 0.053 mmol, 1% per C-Br bond) , was added degassed K2CO3 aqueous (20 mL) and degassed toluene (50 mL) . The solution was refluxed under N2 protection for 24 h. The resulting brown solution was extracted with CH2Cl2 (50 mL x 4) . The combined organic layers were dried over MgSO4 and evaporated under reduced pressure to remove the solvent. The residue was then purified with a silicon gel column using CH2Cl2/hexane (1:4.5) as the eluent to obtain the desired product as a yellow solid (4.26 g, 95% yield) . 1H NMR (400 MHz, CDCl3) : δ (ppm) 8.03 (d, 2H, J = 0.8 Hz), 7.83 (dd, 2H, J = 7.6, 1.2 Hz), 7.78 (dd, 2H, J = 7.6 Hz), 7.74 (dd, 2H, J = 7.6, 1.2 Hz), 7.60 - 7.66 (m, 6H), 7.31 - 7.37 (m, 6H), 2.02 (t, 8H, J = 8.0 Hz), 1.06 - 1.16 (m, 24 H), 0.76 (t, 12H, J = 7.2 Hz), 0.66 (hexa, 8H, J = 6.8 Hz) . MS (MALDI) : m/z = 844.71 (calcd. for C63H72O: 844.57) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 110℃; Inert atmosphere; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 110℃;Inert atmosphere; | A mixture of (9,9-di--hexyl-9H-fluoren-2-yl)boronic acid [J. Am. Chem. Soc, 2004, 126, 13695-13702] (500 mg, 1.32 mmol), 7-bromobenzo[c] [l,2,5]thiadiazole-4-carbaldehyde [J. Am. Chem. Soc, 2004, 126, 13695- 13702] (258 mg, 1.06 mmol), potassium carbonate (680 mg, 12.1 mmol) in toluene (10 mL), ethanol (4 mL), and water (6 mL) was sparged with argon for 10 mins. Tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol) was added and the solution heated in an oil bath held at 110 C overnight under a blanket of argon. The solution when then cooled, diluted with water (100 mL), diethyl ether (100 mL), and the layers separated. The aqueous solution was extracted with diethyl ether (4 x 50 mL), and the combined organic extracts washed with water (2 x 50 mL), brine (50 mL), dried over anhydrous sodium sulphate, filtered, and the solvent removed in vacuo. The crude reside was initially purified by column chromatography over silica using a dichloromethane: light petroleum mixture (3: 10 to 4:5) as eluent to afford an orange solid. The solid was recrystallised from dichloromethane and methanol to afford AL03-96 as a bright orange solid (445 mg, 84%). 1H NMR (500 MHz, CDC13) delta: 0.66-0.81 (10H, m, HexH), 1.01- 1.17 (12H, m, HexH), 1.96-2.12 (8H, m, HexH), 7.34-7.42 (3H, m, FIH), 7.76-7.81 (1H, m, FIH), 7.88 (1H, dd, = 0.5, 8.0 Hz, FIH), 7.96 (1H, dd, = 0.5, 7.5 Hz, BTH), 7.99 (1H, dd, = 0.5, 2.0 Hz, FIH), 8.03 (1H, dd, = 2.0, 8.0 Hz, FIH), 8.34 (1H, d, = 7.5 Hz, BTH), 10.81 (1H, s, CHO). HRMS (ESI-MS) for C32H36N2OS [M + Na]+ Calcd: 497.2621 (100%), 498.2655 (35%). Found: 497.2604 (100%), 498.2634 (36%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃;Inert atmosphere; | A mixture of (9,9-di-n-hexyl-9H-fluoren-2-yl)boronic acid [J. Am. Chem. Soc, 2004, 126, 13695-13702] (915 mg, 2.42 mmol), 4-bromobenzo[c] [l,2,5]thiadiazole [J. Phys. Chem. B, 2012, 116, 7259-7268] (434 mg, 2.02 mmol), and potassium carbonate (1.20 g, 8.70 mmol) in toluene (20 mL), ethanol (8 mL), and water (12 mL) was placed under vacuum until boiling and backfilled with argon six times. Tetrakis(triphenylphosphine)- palladium(O) (100 mg, 0.087 mmol) was added and the solution heated in an oil bath held at 100°C overnight under a blanket of argon. The solution when then cooled, diluted with water (90 mL), diethyl ether (90 mL), brine (60 mL), and the layers separated. The aqueous solution was extracted with diethyl ether (3 x 60 mL) and the combined organic extracts were washed with water (2 x 60 mL), brine (60 mL), dried over anhydrous magnesium sulphate, filtered on a silica plug, and the solvent removed in vacuo. The crude residue was purified by column chromatography over silica using a dichloromethane: light petroleum mixture (0: 1 to 1 : 10) as eluent to afford AL03-77 as yellow/green oil after removal of the solvent (751 mg, 79percent). 1H NMR (500 MHz, CDC13) delta: 0.66-0.83 (10H, m, HexH), 1.00- 1.12 (12H, m, HexH), 1.95-2.09 (4H, m, HexH), 7.31- 7.40 (3H, m, FIH), 7.71 (1H, dd, = 8.5, 8.5 Hz, BTH), 7.76 (2H, dd, = 1.0, 7.0 Hz, FIH), 7.85 (1H, dd, = 0.5, 8.0 Hz, BTH), .90 (1H, d, = 0.5 Hz, BTH), 7.97 (1H, dd, = 1.5, 8.0 Hz, FIH), 8.00 (1H, dd, = 1.0, 8.5 Hz, FIH). HRMS (ESI-MS) for C31H36N2S [M + Na]+ Calcd: 491.2491 (100percent), 492.2522 (34percent), 493.2511 (10percent). Found: 491.2491 (100percent), 492.2500 (40percent), 493.2480 (12percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate | |
57% | With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate Inert atmosphere; Schlenk technique; |