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CAS No. : | 852619-28-4 | MDL No. : | MFCD05864647 |
Formula : | C6H5BrO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HURJBJVXFHMXNU-UHFFFAOYSA-N |
M.W : | 237.07 | Pubchem ID : | 52911197 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
73% | With selenium(IV) oxide In 1,4-dioxane; water for 15.25 h; Heating / reflux | A mixture of selenium dioxide (8.66 g, 78 mmol), water (2.8mL) and 1,4-dioxane (75mL) was heated to reflux to dissolve all particulates (-15 min) before the addition of 2-acetyl- 5-bromothiophene(8 g, 39 mmol) in one portion. After refluxing for 15 hrs, the mixture was cooled to ambient temperature, filtered through diatomaceous earth (1.5" by 3"diameter), washed liberally with Et2O, and concentrated in vacuo to a yellow residue. The residue was subjected to Kugelrohr distillation (150 C/1 Torr) to yield a glyoxal as a yellow oil, which was immediately added to boiling water. Recrystallization from water, filtration, and drying (37 C and 5 Torr) yielded the glyoxal hydrate,1- (5-bromo-thiophen-2-yl)-2, 2- dihydroxyethanone, as white-pink needles (6.723 g,73percent). 1H NMR (300 MHz, DMSO-d6)6 5.43 (t, J= 6.1 Hz,1H), 6.93 (d, J= 6. 1 Hz, 2H), 7.37 (d, J= 4.1 Hz, 1H), 7.81 (d, J= 4.1 Hz, 1H);13C NMR (300 MHz, DMSO-d6) 6 90.28, 122.32, 132.23,135. 73,141. 15,189. 6. |
73% | With selenium(IV) oxide In 1,4-dioxane; water for 15.25 h; Heating / reflux | A mixture of selenium dioxide (8.66 g, 78 mmol), water (2.8 mL) and 1,4-dioxane (75 mL) was heated to reflux to dissolve all particulates(~15 min) before the addition of 2-acetyl- 5-bromothiophene (8 g, 39 mmol) in one portion. After refluxing for 15 hrs, the mixture was cooled to ambient temperature, filtered through diatomaceous earth (1.5" by 3"diameter), washed liberally withEt2O, and concentratediiz vacuo to a yellow residue. The residue was subjected to Kugelrohr distillation(150 C/1 Torr) to yield a glyoxal as a yellow oil, which was immediately added to boiling water. Recrystallization from water, filtration, and drying(37 C and 5 Torr) yielded the glyoxal hydrate,1- (5-bromo-thiophen-2-yl)-2, 2- dihydroxyethanone, as white-pink needles (6.723 g, 73percent). 1H NMR (300 MHz, DMSO-d6) 6 5.43 (t,J= 6.1 Hz,1H), 6. 93 (d,J= 6.1 Hz, 2H), 7.37 (d,J= 4.1 Hz, 1H), 7.81 (d,J= 4.1 Hz, 1H);13C NMR (300 MHz, DMSO-d6) 6 90.28, 122.32, 132.23,135. 73,141. 15, 189. 6. |
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