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HazMat fee for 500 gram (Estimated)
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USD 0.00
Limited Quantity
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USD 80+
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Structure of 607-58-9 * Storage: {[proInfo.prStorage]}
* 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.
With potassium carbonate In acetonitrile at 125℃; for 0.333333 h; Microwave irradiation
General procedure: A mixture of 0.14 g (1.0 mmol) of 1- and 2-naphthol (1)and (6), in most cases 1.0 mmol of alkali carbonate (0.14 g of K2CO3 or 0.33 g of Cs2CO3), in certain cases 11.4 mg(0.05 mmol) of TEBAC and 1.2 mmol of alkyl halide (0.14ml of benzyl bromide, 0.10 ml of ethyl iodide, 0.12 mol ofbutyl bromide or 0.11 ml of i-propyl bromide) in a closedvial was irradiated (20–30 W) in a CEM Discover [300 W]MW reactor at 125 °C for the appropriate time. The reactionmixture was taken up in 25 ml of ethyl acetate and the suspensionwas filtered. Evaporation of the volatile componentsprovided the crude product that was passed through a thin(ca. 2–3 cm) layer of silica gel using ethyl acetate as theeluant to give an oil that was analysed by GC–MS or GC.Similar reactions were carried out in 3 ml of MeCN asthe solvent. The work-up was similar to that described forthe solventless alkylations above, but in this case, ethyl acetatedid not have to be added.The major components of the above reactions, such ascompounds 2, 7, 8, 10a-c and 13a,b were obtained in a pureform by repeated chromatography.Control experiments were performed with benzyl bromidein a similar way under conventional heating.
86%
With potassium phosphate; tetrabutylammomium bromide In water at 20℃; for 2 h; Sealed tube; Green chemistry
General procedure: General procedure for benzylation of phenols: Phenol (0.5mmol), benzyl bromide (1.2equiv), TBAB (0.5equiv), K3PO4 (1.5equiv), and water (2mL) were added to a reaction vessel. The mixture was stirred at room temperature for 2h under air. After the reaction was completed, the mixture was diluted with water and extracted with CH2Cl2 (15mL×3). The combined organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by thin layer chromatography (TLC) on silica gel GF254 (ethyl acetate/petroleum ether) to give the pure product.
Reference:
[1] Letters in Organic Chemistry, 2013, vol. 10, # 5, p. 330 - 336
[2] Chemistry - A European Journal, 2016, vol. 22, # 42, p. 15058 - 15068
[3] Tetrahedron, 2014, vol. 70, # 16, p. 2669 - 2673
[4] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1027 - 1035
[5] Journal of Organic Chemistry, 2009, vol. 74, # 3, p. 1367 - 1370
[6] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 4, p. 1371 - 1385
[7] Tetrahedron, 2000, vol. 56, # 36, p. 6913 - 6925
[8] Organic Letters, 2011, vol. 13, # 16, p. 4340 - 4343
[9] Green Chemistry, 2015, vol. 17, # 7, p. 3910 - 3915
2
[ 90-15-3 ]
[ 53772-44-4 ]
[ 607-58-9 ]
Reference:
[1] Chemistry Letters, 2003, vol. 32, # 1, p. 22 - 23
[2] Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1645 - 1667
[3] Journal of the American Chemical Society, 2004, vol. 126, # 23, p. 7359 - 7367
3
[ 3019-88-3 ]
[ 100-44-7 ]
[ 607-58-9 ]
Reference:
[1] Journal of the American Chemical Society, 1986, vol. 108, # 10, p. 2637 - 2640
4
[ 90-15-3 ]
[ 100-39-0 ]
[ 28178-96-3 ]
[ 607-58-9 ]
Yield
Reaction Conditions
Operation in experiment
62 %Chromat.
With caesium carbonate In neat (no solvent) at 125℃; for 1 h; Microwave irradiation
General procedure: A mixture of 0.14 g (1.0 mmol) of 1- and 2-naphthol (1)and (6), in most cases 1.0 mmol of alkali carbonate (0.14 g of K2CO3 or 0.33 g of Cs2CO3), in certain cases 11.4 mg(0.05 mmol) of TEBAC and 1.2 mmol of alkyl halide (0.14ml of benzyl bromide, 0.10 ml of ethyl iodide, 0.12 mol ofbutyl bromide or 0.11 ml of i-propyl bromide) in a closedvial was irradiated (20–30 W) in a CEM Discover [300 W]MW reactor at 125 °C for the appropriate time. The reactionmixture was taken up in 25 ml of ethyl acetate and the suspensionwas filtered. Evaporation of the volatile componentsprovided the crude product that was passed through a thin(ca. 2–3 cm) layer of silica gel using ethyl acetate as theeluant to give an oil that was analysed by GC–MS or GC.Similar reactions were carried out in 3 ml of MeCN asthe solvent. The work-up was similar to that described forthe solventless alkylations above, but in this case, ethyl acetatedid not have to be added.The major components of the above reactions, such ascompounds 2, 7, 8, 10a-c and 13a,b were obtained in a pureform by repeated chromatography.Control experiments were performed with benzyl bromidein a similar way under conventional heating.
Reference:
[1] Letters in Organic Chemistry, 2013, vol. 10, # 5, p. 330 - 336
With potassium carbonate; In acetonitrile; at 125℃; for 0.333333h;Microwave irradiation;
General procedure: A mixture of 0.14 g (1.0 mmol) of 1- and 2-naphthol (1)and (6), in most cases 1.0 mmol of alkali carbonate (0.14 g of K2CO3 or 0.33 g of Cs2CO3), in certain cases 11.4 mg(0.05 mmol) of TEBAC and 1.2 mmol of alkyl halide (0.14ml of benzyl bromide, 0.10 ml of ethyl iodide, 0.12 mol ofbutyl bromide or 0.11 ml of i-propyl bromide) in a closedvial was irradiated (20-30 W) in a CEM Discover [300 W]MW reactor at 125 C for the appropriate time. The reactionmixture was taken up in 25 ml of ethyl acetate and the suspensionwas filtered. Evaporation of the volatile componentsprovided the crude product that was passed through a thin(ca. 2-3 cm) layer of silica gel using ethyl acetate as theeluant to give an oil that was analysed by GC-MS or GC.Similar reactions were carried out in 3 ml of MeCN asthe solvent. The work-up was similar to that described forthe solventless alkylations above, but in this case, ethyl acetatedid not have to be added.The major components of the above reactions, such ascompounds 2, 7, 8, 10a-c and 13a,b were obtained in a pureform by repeated chromatography.Control experiments were performed with benzyl bromidein a similar way under conventional heating.
86%
With potassium phosphate; tetrabutylammomium bromide; In water; at 20℃; for 2h;Sealed tube; Green chemistry;
General procedure: General procedure for benzylation of phenols: Phenol (0.5mmol), benzyl bromide (1.2equiv), TBAB (0.5equiv), K3PO4 (1.5equiv), and water (2mL) were added to a reaction vessel. The mixture was stirred at room temperature for 2h under air. After the reaction was completed, the mixture was diluted with water and extracted with CH2Cl2 (15mL×3). The combined organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by thin layer chromatography (TLC) on silica gel GF254 (ethyl acetate/petroleum ether) to give the pure product.
With palladium diacetate; sodium hydride; In N,N-dimethyl acetamide; at 50℃; for 5h;Inert atmosphere;
Palladium acetate (3.4 mg, 0.015 mmol, 5 mol%) and sodium hydride (60% in oil, 18 mg, 0.45 mmol, 1.5 equiv) were suspended in DMA (1.0 mL) under nitrogen.After stirring at 25 C for 5 minutes, a solution of Compound 1 (0.3 mmol) in DMA (0.5 mL) was added, followed by a reaction at 50 C for 5 hours.The reaction was stopped by adding ice water, the pH was adjusted to 3.5 with dilute hydrochloric acid, and extracted with ethyl acetate.Drying with sodium sulfate, rotary evaporation and purification by column chromatography gave product 2, yield 98%.
93%
With bis(2-hydroxyethyl)ammonium formate; palladium dichloride; at 20℃; for 12h;Inert atmosphere;
To a solution of nitrobenzene (9) (123 mg, 1.00 mmol) in [BHEA][HCO2] (5.00 mL, 39.7 mmol)was added PdCl2 (1.80 mg, 1.00 mol %) at rt and the reaction mixture was stirred at the same temperature for 12 h under argon atmosphere. The mixture was poured into brine (10 mL) and extracted with EtOAc (10 10 mL). The organic layer was washed with brine (150 mL) and dried with MgSO4. To a solution was added acetic anhydride (2.84 mL, 30 mmol) at rt and the reaction mixturewas stirred at the same temperature for 30 min under argon atmosphere. The mixture was washed with a saturated solution of sodium carbonate (80 mL), brine (150 mL), and dried with MgSO4. After removal of the solvent, the residue was subjected to column chromatography (Merck Kieselgel 60, Phi=2.0 cm, l=11.5 cm; EtOAc-hexane, 1:3) to give acetanilide (22); yield: 130 mg (96%).
With caesium carbonate; In neat (no solvent); at 125℃; for 1h;Microwave irradiation;
General procedure: A mixture of 0.14 g (1.0 mmol) of 1- and 2-naphthol (1)and (6), in most cases 1.0 mmol of alkali carbonate (0.14 g of K2CO3 or 0.33 g of Cs2CO3), in certain cases 11.4 mg(0.05 mmol) of TEBAC and 1.2 mmol of alkyl halide (0.14ml of benzyl bromide, 0.10 ml of ethyl iodide, 0.12 mol ofbutyl bromide or 0.11 ml of i-propyl bromide) in a closedvial was irradiated (20-30 W) in a CEM Discover [300 W]MW reactor at 125 C for the appropriate time. The reactionmixture was taken up in 25 ml of ethyl acetate and the suspensionwas filtered. Evaporation of the volatile componentsprovided the crude product that was passed through a thin(ca. 2-3 cm) layer of silica gel using ethyl acetate as theeluant to give an oil that was analysed by GC-MS or GC.Similar reactions were carried out in 3 ml of MeCN asthe solvent. The work-up was similar to that described forthe solventless alkylations above, but in this case, ethyl acetatedid not have to be added.The major components of the above reactions, such ascompounds 2, 7, 8, 10a-c and 13a,b were obtained in a pureform by repeated chromatography.Control experiments were performed with benzyl bromidein a similar way under conventional heating.