Background and overview of preparation and application of 10-(2-naphthyl)anthracene-9-boronic acid
10-(2-naphthyl)anthracene-9-boronic acid is an organic intermediate, often used in Suzuki and other metal coupling reactions. 2-bromonaphthalene can be used as the reaction raw material to react with n-butyllithium, and then with 9,10-Dibromoanthracene is coupled and prepared by reaction.
Preparation and application of 10-(2-naphthyl)anthracene-9-boronic acid
Preparation and application of 10-(2-naphthyl)anthracene-9-boronic acid Synthesis of intermediate-1
Under nitrogen protection conditions, dissolve 2.07g, 10mmoL of 2-bromonaphthalene in 40mL of anhydrous tetrahydrofuran, lower the temperature of the reactant to -78°C, slowly add 4mL of 2.5M n-butyllithium dropwise, and react. The mixture was stirred at 0°C for 1 hour, then the temperature of the reactant was lowered to -78°C, 12.47g of 12 mmol trimethyl borate was added dropwise, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with diethyl ether.
Remove the moisture in the organic layer with anhydrous magnesium sulfate, filter with suction, and concentrate the organic solution. The compound obtained is passed through the chromatography column with the eluent of Hex:EA=5:1 to obtain 1.48g (86%) of Intermediate-1. .
Preparation and application of 10-(2-naphthyl)anthracene-9-boronic acid and synthesis of intermediate-7
Under nitrogen protection, add 3.36g, 10mmol of 9,10-dibromoanthracene and 1.72g, 10mmol of intermediate-1, dissolve in 40mL of toluene, and add 0.58g, 0.5mmol of Pd (PPh3) respectively. 4 and 15 mL, 30 mmol of 2MK2CO3, reflux for 24 hours. After the reaction is completed, the temperature of the reactants is reduced to normal temperature, 200 mL of MC and 200 mL of H2O are added, the MC layer is extracted, dried and concentrated with anhydrous magnesium sulfate, and passed through the chromatography column with an eluting calcium bicarbonate solution of Hex:EA=4:1 to obtain the intermediate Body – 72.45g (64%).
Preparation and application of 10-(2-naphthyl)anthracene-9-boronic acid Synthesis of 10-(2-naphthyl)anthracene-9-boronic acid
Under nitrogen protection conditions, dissolve 3.83g, 10mmol of Intermediate-7 in 40mL of anhydrous tetrahydrofuran, lower the temperature of the reactant to -78°C, slowly add 4mL of 2.5M n-butyllithium, and the reactant Stir at 0°C for 1 hour, then lower the temperature of the reactant to -78°C, add 12.47g of 12 mmol of trimethyl borate dropwise, and stir at room temperature for 12 hours. After the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with diethyl ether. Use anhydrous magnesium sulfate to remove the moisture in the organic layer, filter with suction, and concentrate the organic solution. The compound obtained is passed through a chromatography column using the eluent of Hex:EA=3:1 to obtain 3.10g (89%) of Intermediate-10.
Preparation and application of 10-(2-naphthyl)anthracene-9-boronic acid
1 Lanthanum carbonate 0-(2-naphthyl)anthracene-9-boronic acid can undergo Suzuki coupling reaction: 1,3-bis[2-(5-bromopyridine)]-benzene ( 200 mg, 0.512 mmol), [10-(2-naphthalene)9-anthracene]boronic acid (273 mg, 1.23 mmol), tetrakis(triphenylphosphine)palladium (29.6 mg, 0.026 mmol), toluene (80 mL) and aqueous potassium carbonate solution (40mL, 2M), put it into a 250ml three-necked round-bottomed flask, stir, and the mixture was heated to 90°C under the protection of nitrogen gas flow for 12 hours. After the reaction was completed, it was naturally cooled to room temperature. The crude product was washed with dichloromethane (40 ml) and deionized water (4/30 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and distilled under reduced pressure to obtain the crude product. The crude product Purify by silica gel column chromatography using dichloromethane and n-hexane as 1:2 developing solvent, and then recrystallize using n-hexane and dichloromethane to obtain 341 mg of white powder, yield: 81%. 1H-NMR (MHz, CDCl3): δ=9.078 (s, 1H), 8.937-8.947 (d, 2H), 8.356-8.380 (dd, 2H), 8.114-8.177 (dd, 6H), 8.056-8.076 (d, 2H), 7.762-7.782 (d, 6H), 7.600-7.764 (t, 2H), 7.518-7.559 (t, 6H), 7.427-7.465 (t, 4H), 7.182- 7.331(m,9H);
References
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