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CAS No. : | 1812221-73-0 | MDL No. : | MFCD27976157 |
Formula : | C9H7BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FUMLPTOXTGCROI-UHFFFAOYSA-N |
M.W : | 227.05 g/mol | Pubchem ID : | 118407465 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
Multi-step reaction with 2 steps 1.1: trimethylaluminum / toluene; dichloromethane / 0.25 h / 0 - 20 °C 1.2: 3 h / 20 °C 2.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: trimethylaluminum / toluene; dichloromethane / 0.25 h / 0 - 20 °C 1.2: 3 h / 20 °C 2.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 3.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: (2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine With trimethylaluminum In dichloromethane; toluene at 0 - 20℃; for 0.25h; Stage #2: 5-bromo-isochroman-1-one In dichloromethane; toluene at 20℃; for 3h; | 70.1 Step 1 Step 1: A solution of trimethyl aluminum (2 mol/L, 3.85 mL) in toluene was added into a solution of compound70-2 in dry DCM (20 mL) at 0 °C, the reaction mixture was stirred at room temperature for 15 min. Then a solution ofcompound 70-1 (0.7 g, 3.1 mmol) in DCM (5 mL) was added dropwise, and the obtained solution was stirred at roomtemperature for 3h. After the reaction was complete as detected by LCMS, Rochelle salt solution was added. Theobtained mixture was extracted with DCM, washed with brines, dried over anhydrous sodium sulfate, and concentratedEP 3 124 482 A158510152025303540455055under reduced pressure. The residue was purified by silica gel column chromatography (PE/EtOAc= 5:1) to delivercompound 70-3 (1.1 g, 85%) as yellow solid. MS ESI calcd for C20H24BrN3O3 [M+H]+ 435, found 435. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium hexafluorophosphate; Iron(III) nitrate nonahydrate; oxygen; In acetonitrile; at 80℃; for 5.0h; | To 35 ml of in tube sealing, adding 1mmol of 5 - bromine different chroman (formula (1 - 9)), 0.1mmol of Fe (NO3)3· 9H2O, 0.2mmol of KPF6 and 3 ml of acetonitrile, to the oxygen of the air in the of the replacement pipe, for the closed after a rubber plug, is inserted into the oxygen-ball, the reaction bottle into a pre-heated oil bath heated to 80 C, reaction 5h. Filtration, filtrate is decompressed and evaporate the solvent, and then the column chromatography, using ethyl acetate/petroleum ether volume ratio 1:50 of the mixed solution is the eluant, collecting the eluant containing the compound, evaporate the solvent to obtain the product 5 - bromine different chroman -4 - one, separating the yield is 90%. |
90% | With oxygen; nitric acid; In acetonitrile; at 140℃; under 22801.5 Torr; for 18.0h;Catalytic behavior; | General procedure: After an about 45 mL glass tube was charged with 2 mL acetonitrile, 0.5 mmol substrate and 0.075 mmol HNO3, the system was flushed with oxygen gas three times. Subsequently, the reaction tube was sealed and heated with magnetic stirring at 140 C for 3 h. When the reaction time was reached, the reaction mixture was cooled to room temperature. Finally, evaporation of solvent followed by column chromatography yielded the targeted product. GC yields were obtained by the GC analysisof the mixture from another parallel experiment. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With [Cu(salicylate)2(NCMe)]2; tetrabutyl-ammonium chloride; oxygen In 1,2-dimethoxyethane at 60℃; for 12h; Schlenk technique; | 7 Example 1 General procedure: Under oxygen atmosphere,1.0 mg (0.0014 mmol) of binuclear salicylic acid copper complex,0.9 mg (0.0028 mmol) tetrabutylammonium chloride (TBAC),134 mg (1 mmol) isochroman,1.0mL ethylene glycol dimethyl ether added Scheck tube,The reaction was stirred at 60 ° C for 12 hours,When the reaction is over,To the mixture was added 10 mL of distilled water,Then extracted with 15mL dichloromethane three times,The organic phase was collected, dried over anhydrous Na2SO4,Suction filtration,Dichloromethane was removed on a rotary evaporator,Column chromatography to obtain a colorless oily isochromate, the yield was 70%, |
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