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CAS No. : | 1528607-78-4 | MDL No. : | MFCD22381231 |
Formula : | C8H5BrF2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAOKHDWJQCHTID-UHFFFAOYSA-N |
M.W : | 235.03 | Pubchem ID : | 83410729 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-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 |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium acetate / ethanol; water / 3 h / 70 °C 2.1: borane-THF / tetrahydrofuran / 212.17 h / 70 °C 2.2: 1 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27.7 g | With sodium acetate In ethanol; water at 70℃; for 3h; | Intermediate 62: To a mixture of 26 g (110 mmoles) of intermediate 61 in 53 mL of ethanol there are added 107 mL of water, 11.8 g (141 mmoles) of methoxylamine hydrochloride and 11.8 g (142 mmoles) of sodium acetate. The mixture is heated for 3 hours at 70° C. The mixture is returned to ambient temperature and then extracted with AcOEt (0.5 L) in the presence of a saturated aqueous NaCl solution. The organic phase is dried over MgSO4. Evaporation under reduced pressure yields 27.7 g of the mixture of oximes 62 in the form of a light-brown solid, which is used without additional treatment in the following step. IR (cm-1): 1025 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.5 g | Stage #1: C8H5BrF2O; methylamine hydrochloride With titanium(IV) isopropylate; triethylamine In ethanol at 20℃; for 40h; Stage #2: With sodium tetrahydroborate In ethanol for 20h; | Intermediate 211: To a mixture of TiOiPr4 (16 mL, 54 mmoles) in ethanol (70 mL) there are added NEt3 (7.7 mL, 55.3 mmoles), methylamine hydrochloride (3.7 g, 54.8 mmoles) and intermediate 61 (7 g, 27.8 mmoles). The mixture is stirred at ambient temperature for 40 hours, and then NaBH4 (1.56 g, 41.4 mmoles) is added in portions. After 20 hours' stirring, the reaction mixture is poured carefully into a 2N aqueous NH4OH solution, and the resulting precipitate is filtered off and rinsed with methylene chloride. The filtrate is decanted, the organic phase is washed with a 2N aqueous HCl solution, and the acidic phase is brought to basic pH by means of a 20% sodium hydroxide solution. The product is extracted with methylene chloride, the organic phase is dried over MgSO4, and evaporation under reduced pressure yields an oil, which is purified on silica gel using a methylene chloride/ethanol elution gradient 100/0 to 95/5. Intermediate 210 is isolated in the form of an oil (1.5 g). 1H NMR (400 MHz; DMSO-d6): δ 7.25 (d, 2H), 3.6 (q, 1H), 2.5-2.15 (m, 1H), 2.10 (s, 3H), 1.20 (d, 3H) IR (cm-1): 3280-3360 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3.1: lithium dipropan-2-ylazanide / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: sodium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: sodium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 20 °C 3: lithium dipropan-2-ylazanide / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: sodium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 20 °C 3: lithium dipropan-2-ylazanide / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere 4: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: sodium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 20 °C 3: lithium dipropan-2-ylazanide / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere 4: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere 5: Lux Cellulose-4 / Supercritical conditions; Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: sodium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 20 °C 3: lithium dipropan-2-ylazanide / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere 4: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere 5: Lux Cellulose-4 / Supercritical conditions; Resolution of racemate 6: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 6 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: sodium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 20 °C 3: lithium dipropan-2-ylazanide / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere 4: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 100 °C / Inert atmosphere 5: Lux Cellulose-4 / Supercritical conditions; Resolution of racemate 6: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 6 h / 40 °C 7: N,N-dimethyl-4-aminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 16 h / 20 - 25 °C / Inert atmosphere |
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