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CAS No. : | 153435-80-4 | MDL No. : | MFCD07363826 |
Formula : | C8H10BrNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RHBJVOGENJVLGT-UHFFFAOYSA-N |
M.W : | 264.14 | Pubchem ID : | 7129845 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
86% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride; In 1,2-dimethoxyethane; at 80℃; for 20h;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube was dried under vacuum, filled with nitrogen and charged consecutively with 1.00 eq bromine substrate, 1.00 eq boronic acid, 2.10 eq CsF, 0.05 eq PdCl2(dppf)*DCM and anhydrous DME (2 mL/0.15 mmol bromoarene). The suspension was degassed by vacuum/N2 cycles and stirred at 80 C. As TLC analysis or GC-MS analysis indicated full conversion of the starting material, the reaction mixture was cooled to rt and filtered through a pad of celite, which was rinsed with EtOAc and/or DCM. The solvent from the filtrate was removed under reduced pressure and final purification by column chromatography or silica gel filtration yielded the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90.0℃; for 12.0h;Inert atmosphere; | To a stirred solution of 3-bromo-N,N-dimethylbenzene-l-sulfonamide (0.350 g, 1.33 mmol) and 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (0.505 g, 1.99 mmol) in 1,4-dioxane (5 mL) was added potassium acetate (0.263 g, 2.65 mmol). Then the reaction mixture was degassed under argon gas for 10 minutes. This was followed by the addition of [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.097 g, 0.133 mmol) and the reaction mixture was heated to 90 C for 12 hours. After completion of the reaction, the reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (2 x20 ml). The organic phase was washed with water, brine solution and dried over anhydrous sodium sulfate, concentrated in vacuo to afford N, A-dimcthyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenes sulfonamide as a brown solid ( 0.2 g, crude); The crude material was used as such for next step without column purification. |
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