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CAS No. : | 144292-32-0 | MDL No. : | MFCD08061907 |
Formula : | C6H3BrF2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JZAVCMMYGSROJP-UHFFFAOYSA-N |
M.W : | 208.99 | Pubchem ID : | 10219942 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
With sodium carbonate;palladium on activated charcoal; In isopropyl alcohol; for 10h;Reflux; Inert atmosphere; | In a reactor under nitrogen atmosphere, 20.0 g of compound (a2)17.2 g of 4-bromo-2,3-difluorophenol (a3), 30.6 g of sodium carbonate, 0.54 g of palladium on carbon catalyst (Pd/C) were dissolved in 120 mL of 2-propanol (IPA). After stirring by refluxing for 10 hours, the reaction mixture was cooled to room temperature, and injected into a mixture of 500 ml of 1N hydrochloric acid and 300 ml of toluene which was cooled into 0 C. The mixture was separated into organic layer and aqueous layer and the organic layer was extracted. The resulting organic layer was washed with saturated chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to provide the residue. The resulting residue was purified by recrystallization from heptan, dried to provide 13.2 g of 4'-ethoxy-2,3,2',3'-tetrafluorobiphenyl-4-ol (a4) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrabutylammomium bromide; sodium hydroxide; In water; at 80℃; for 6h;Inert atmosphere; | To an aqueous (400 ml) solution of 4-bromo-2,3-difluorophenol (T-1) (195.0 g), bromoethane (196.2 g) and tetrabutylammonium bromide (hereinafter, abbreviated as TBAB) (24.2 g), sodium hydroxide (75.9 g) was added, and heating agitation was carried out at 80 C for 6 hours in a nitrogen atmosphere. After completion of the reaction, extraction was carried out with heptane, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a black oily matter was obtained. The resultant material was purified by distillation, and thus 1-ethoxy-2,3-difluorobromobenzene (T-2) was obtained as a colorless oily matter (230.0 g, yield: 97%). |
97% | With tetrabutylammomium bromide; sodium hydroxide; In water; at 80℃; for 6h;Inert atmosphere; | To a water (400 ml) solution of 4-bromo-2,3-difluorophenol (T-1) (195.0 g), bromoethane (196.2 g) and tetrabutylammonium bromide (hereinafter referred to as TBAB) , Sodium hydroxide (75.9 g) were added, and the mixture was heated and stirred at 80 C. for 6 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with heptane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a black oil. This product was purified by distillation to give 1-ethoxy-2,3-difluorobromobenzene (T-2) as a colorless oil (230.0 g, yield 97%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In N,N-dimethyl-formamide; for 72h; | Methyl iodide (1.56 mL, 25.1 mmol, 1.5 equ) was added dropwise to a suspension of 4-bromo- 2,3-difluorophenol (3.5 g, 16.7 mmol) and potassium carbonate (2.77 g, 20.0 mmol, 1.2 equ) in N,N-dimethylformamide (30 mL) and the mixture was stirred for 3 days. The precipitate was removed by filtration and the filtrate was concentrated to dryness in vacuo. Dichloromethane and water were added and the product was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to give l-bromo-2,3- difluoro-4-methoxybenzene as a white crystalline solid (3.8 g, quantitative). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With boron tribromide; In dichloromethane; at -20 - 20℃; for 12h; | To a stirred solution of l-bromo-2,3-difluoro-4-methoxybenzene (3 g, 13.45 mmol) in DCM (30 mL) at -20 C was added 1M BBr3 in DCM (26.9 mL, 26.9 mmol) dropwise over 10 min. The cold bath was removed and the reaction mixture was stirred at RT for 12 h. The reaction mixture was cooled to 10 C and quenched with saturated aqueous sodium bicarbonate solution (100 mL). The mixture was diluted with DCM (150 mL). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure to afford 4-bromo-2,3- difiuorophenol (2 g, 9.47 mmol, 70% yield) as a dark red oil. NMR (400 MHz, CHLOROFORM-cf): delta 7.15-7.21 (m, 1H), 6.69-6.76 (m, 1H), 5.30-5.31 (m, 1H) ppm. |
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