CAS No. : | 27329-70-0 | MDL No. : | MFCD01114696 |
Formula : | C5H5BO4 | Boiling Point : | - |
Linear Structure Formula : | HCOC4H2OB(OH)2 | InChI Key : | JUWYQISLQJRRNT-UHFFFAOYSA-N |
M.W : | 139.90 | Pubchem ID : | 2734355 |
Synonyms : |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501 | UN#: | 3077 |
Hazard Statements: | H315-H318-H335-H411 | Packing Group: | Ⅲ |
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 |
---|---|---|
75% | A dried 500 mL 3-neck flask with mechanical stirrer, internal thermometer and addition funnel under nitrogen is charged with 20,16 g (0,118 mol) furfuraldiethylacetal, 33,4 g (0,177 mol) triisopropylborate and 40 mL of anhydrous THF. The water content of the reaction mixture was measured according to the Karl-Fischer-titration method and was determined to be less than 800 mug/mL of water. The solution is cooled to an internal temperature of -10C. Keeping the temperature at -10C to 0C 84 mL (25 wt%, 1.84 M solution THF, heptane, ethylbenzene from Chemmetal, content determined by titration, 1.3 equivalents) LDA was added via addition funnel to the reaction mixture over a period of 1 hour. Using a canula the reaction mixture was subsequently transferred to precooled aqueous hydrochloric acid which was obtained by mixing 33 mL of concentrated hydrochloric acid and 55 mL water. The reaction temperature was maintained at a temperature of less than 30C. The resulting tan slurry of 5-formyl-2-furylboronic acid was cooled to 0C and filtered. The filter cake was washed twice with 20 mL of cold water to give 17.6 g of wet cake. Drying (40C, vacuum oven) gave 12.41 g of an off-white product. The overall yield of 5-formyl-2-furylboronic acid was 75%. The content of unreacted furfural in the crude product was determined to be less than 0,1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 20 - 60℃;Inert atmosphere; | A mixture of <strong>[2051-99-2]1-bromo-4-isobutylbenzene</strong> (1.500 g, 7.04 mmol), 5-formyl-2-furanoboronic acid (1.477, 10.56 mmol) and sodium carbonate (3.134 g, 29.57 mmol) in a mixture of 1,2-dimethoxyethane (75 mL), ethanol (30 mL) and water (15 mL) was vigorously stirred and the reaction flask was purged with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.404 g, 0.35 mmol) was added and the reaction mixture was heated at 60 C. for 3 h. The mixture was allowed to cool to room temperature and was left aside for 4 days. The reaction mixture was diluted with ether (200 mL) and washed successively with water (2×100 mL) and brine. The organic layer was separated, dried over sodium sulfate and concentrated. The residue was chromatographed on flash Silica, eluted with 5 to 10% ethyl acetate in hexanes to afford 5-(4-isobutyl-phenyl)-furan-2-carbaldehyde (490 mg, 31%). 1H NMR (400 MHz, CDCl3): 0.92 (6H, d, J=6.4 Hz), 1.90 (1H, m), 2.51 (2H, d, J=7.2 Hz), 6.80 (1H, d, J=3.6 Hz), 7.20 (2H, m), 7.31 (1H, dd, J=3.6, 1.2 Hz), 7.74 (2H, m), 9.63 (1H, s). ESI-MS: 227.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.6% | With palladium 10% on activated carbon; triethylamine; In methanol; 1,2-dimethoxyethane; at 20 - 45℃; for 3h; | At room temperature (20 ~ 25 C) to 3.5g (14.3mmol) 2- amino-5-iodobenzonitrile (compound of formula III), 3.1g (28.1mmol) 2-formylfuran-5-boronic acid was added to the three-necked flask, was added 70mL of ethylene glycol dimethyl ether, stirred at room temperature suspension system; The 4.4g (43.5mmol) of triethylamine was added to the reaction system, and 0.18g10% Pd / C was dissolved in methanol 35mL disposable Was added to the reaction system, stirring was warmed to 40 ~ 45 C the reaction; TLC trace (eluent, ethyl acetate / dichloromethane = 2/ 1, V / V, UV254nm color) to the starting material disappeared after stopping the reaction (about 3h). Filtered to remove Pd / C, to obtain a reddish black filter Solution, and the filtrate was washed with 100mL water, once with ethyl acetate (50mL * 2) The aqueous phase was extracted twice, the combined organic phases with saturated Brine (80mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to give a white solid 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile (IV compound of the formula) 3.0g (14.1mmol, molar yield of 98.6%, HPLC purity 98.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | At room temperature (20 ~ 25 C) to 9.2g (37.7mmol) 2- amino-5-iodo-benzonitrile (compound of formula III), 8.3g (75.2mmol) 2- Formyl-5-boronic acid was added to the three-necked flask, was added 200mL of ethylene glycol dimethyl ether, stirred at room temperature suspension system; The 11.6g (114.6mmol) of triethylamine was added to the reaction system, the 0.5g10% Pd / C was dissolved in 100mL of methanol disposable Was added to the reaction system, stirring was warmed to 40 ~ 45 C the reaction; TLC trace (eluent, ethyl acetate / dichloromethane = 2/ 1, V / V, UV254nm color) to the starting material disappeared after stopping the reaction (about 3h); filtered to remove Pd / C, to obtain a reddish black filter Solution, the filtrate was transferred to the reaction flask, heated with stirring to 60 C.Weigh toluenesulfonic acid monohydrate 11.5g (60.5mmol), dissolved in 5.0mL water, dubbed p-toluenesulfonic acid solution, The prepared solution of p-toluenesulfonic acid was dropped into the reaction vessel, which was within 20 ~ 30min after the dripping, dripping completed, yellow Colored powdery solid was precipitated, 60 C incubation for 1 hour, the system was slowly cooled to 5 C, 0.5 hours incubation, filtration, A yellow filter cake, the filter cake was rinsed with 20mL of ethylene glycol dimethyl ether, 40 C and dried in vacuo 8h, to give a white solid of 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile p-toluenesulfonic acid(IV compound of the formula) p-toluenesulfonate 13.9g (36.2mmol, 96.0% molar yield, HPLC purity 99.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 65℃; for 1h; | General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 65℃; for 1h; | General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65°C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1). |
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