Alternatived Products of [ 875548-59-7 ]
Product Details of [ 875548-59-7 ]
CAS No. : | 875548-59-7 |
MDL No. : | MFCD26388718 |
Formula : |
C5H6BrNOS
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
208.08
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 875548-59-7 ]
Application In Synthesis of [ 875548-59-7 ]
* 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.
- Upstream synthesis route of [ 875548-59-7 ]
- Downstream synthetic route of [ 875548-59-7 ]
- 1
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[ 464192-28-7 ]
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[ 75-24-1 ]
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[ 875548-59-7 ]
Yield | Reaction Conditions | Operation in experiment |
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In n-heptane; dichloromethane; at 0℃;Inert atmosphere; |
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available <strong>[464192-28-7]2-bromo-thiazole-5-carbaldehyde</strong> (1.80 g, 9.37 mmol) in CH2CI2 (70.0 mL) was treated at 0 0C with trimethylaluminum (46.0 mL of a 1 M solution in heptane, 46 mmol). The reaction mixture was then stirred at 0 0C <n="99"/>for 45 min. CH2CI2 (100.0 ml.) followed by sat. aq. NH4CI (100 ml.) was then added. The mixture was then treated with 1 N HCI (50 ml.) and the aq. layer was extracted with CH2CI2 (150 ml_). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC: rf (1 :2 hept-EA) = 0.40. LC-MS-conditions 02: tR = 0.70 min; [M+AcCN+H]+ = 249.17. |
- 2
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[ 875548-59-7 ]
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[ 1161776-13-1 ]
Yield | Reaction Conditions | Operation in experiment |
92% |
With Dess-Martin periodane; In dichloromethane; at 20℃; for 2h; |
Into a 250-mL round-bottom flask, was placed 1-(2-bromothiazol-5-yl)ethanol (5.792 g, 27.84 mmol), DCM (150 mL), and Dess-Martin reagent (17.72 g, 41.78 mmol). The resulting solution was stirred for 2 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:10 to 1:5). This resulted in5.29 g (92%) of the title compound as an off-white solid. MS-ESI: 207.9, 205.9 (M+1). |
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With manganese(IV) oxide; In acetonitrile; at 25℃;Inert atmosphere; |
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-bromo-thiazol-5-yl)-ethanol (1.95 g, 9.37 mmol) in AcCN (90.0 ml.) was treated at rt with MnO2 (4.53 g, 46.86 mmol) and the reaction mixture was stirred for 16 h at rt before being filtered through Celite. The solvent was removed under reduced pressure to give the title compound as a yellow solid. LC-MS- conditions 02: tR = 0.80 min. |
- 3
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[ 464192-28-7 ]
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[ 75-16-1 ]
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[ 875548-59-7 ]
Yield | Reaction Conditions | Operation in experiment |
77% |
In tetrahydrofuran; at 0℃; for 0.5h;Inert atmosphere; |
Into a 500-mL 3-necked round-bottom flask purged with and maintained under nitrogen, was placed a solution of <strong>[464192-28-7]2-bromothiazole-5-carbaldehyde</strong> (18 g, 93.7 mmol) in THF (200 mL). This was followed by the addition of MeMgBr/THF (3 M, 33 mL) dropwise with stirring at 0C. Theresulting solution was stirred for 0.5 h at 0C. The reaction was then quenched by the addition of200 mL of NH4C1 (sat.). The resulting solution was extracted with 2x200 mL of DCM and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20 to 1:15). This resulted in 15 g (77%) of the title compound as colorless oil. MS-ESI: 209.9, 207.9 (M+1). |