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CAS No. : | 889659-70-5 | MDL No. : | MFCD12546605 |
Formula : | C13H19BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HECOEAIIOZQGFO-UHFFFAOYSA-N |
M.W : | 234.10 | Pubchem ID : | 46739700 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | 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 |
---|---|---|
84% | With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate In 1,4-dioxane; toluene at 95℃; for 16h; Inert atmosphere; | |
68% | With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 80℃; for 3h; | 3.B (B) Synthesis of Compound 33-c In a nitrogen atmosphere, 5.45 g of commercially available Compound 33-b, 1.3 g of dichlorobistriphenylphosphine palladium, 1.08 g of bisdiphenylphosphinoferrocene (dppf), 5.75 g of potassium acetate, 50 ml of dioxane, and 5.0 g of Compound 33-a were mixed, and the mixture was stirred at an outside temperature of 80 C. for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction liquid, for extraction by ethyl acetate. An organic layer was washed with a saturated saline solution, dried over magnesium sulfate, and concentrated, and purified by silica gel column chromatography, to thereby obtain 3.1 g (68% yield) of Compound 33-c. 1H NMR (300 MHz, CDCl3) ? (ppm): 1.34 (12H, s), 2.30 (3H, s), 4.88 (1H,s), 6.79 (1H,s), 7.08 (1H,s), 7.25 (1H,s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; 4-amino-5-bromophthalodinitrile With potassium carbonate; tris-(o-tolyl)phosphine In water; isopropyl alcohol; toluene at 80℃; for 3h; Stage #2: With hydrogenchloride In water; ethyl acetate; isopropyl alcohol; toluene | 3.C (C) Synthesis of Compound 33-d In a nitrogen atmosphere, 3.1 g of Compound 33-c, 2.94 g of Compound 31-e, 3.65 g of potassium carbonate, 0.15 g of palladium acetate, 0.4 g of tri(o-tolyl)phosphine, 15 ml of toluene, 5 ml of water, and 10 ml of isopropyl alcohol were mixed, and the mixture was stirred at an outside temperature of 80 C. for 3 hours. 1M hydrochloric acid and ethyl acetate were added to the reaction liquid, for extraction by ethyl acetate. An organic layer was washed with a saturated saline solution, dried over magnesium sulfate, and concentrated, and purified by silica gel column chromatography, to thereby obtain 2.45 g (74% yield) of Compound 33-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine; dmap / dichloromethane / 3 h / 0 - 20 °C 2: methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate / toluene; 1,4-dioxane / 16 h / 95 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.11 g | Stage #1: 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; ethyl iodide With potassium carbonate In N,N-dimethyl-formamide at 90℃; Stage #2: With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.178 g | Stage #1: 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; isopropyl bromide With potassium carbonate In N,N-dimethyl-formamide at 90℃; Stage #2: With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.228 g | Stage #1: 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; benzyl bromide With potassium carbonate In N,N-dimethyl-formamide at 90℃; Stage #2: With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h; |
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