Alternatived Products of [ 778599-56-7 ]
Product Details of [ 778599-56-7 ]
| CAS No. : | 778599-56-7 |
MDL No. : | |
| Formula : |
C8H8BrNO4
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Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
262.06
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Pubchem ID : | - |
| Synonyms : |
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Safety of [ 778599-56-7 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 778599-56-7 ]
* 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.
- Downstream synthetic route of [ 778599-56-7 ]
- 1
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[ 4920-84-7 ]
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[ 778599-56-7 ]
| Yield | Reaction Conditions | Operation in experiment |
| 89% |
With bromine In chloroform |
|
| 82% |
With N-Bromosuccinimide In neat (no solvent) at 20℃; for 1h; Milling; Green chemistry; regioselective reaction; |
General procedure for synthesis of 2,4-dibromo-1-methoxy-3,5-dimethylbenzene(2b) in ball-milling.
General procedure: 1-Methoxy-3,5-dimethylbenzene(100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reaction was monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetate and cooled at 0 °C. The product was isolated as filtrate upon paper filtration and waste succinimide as precipitate. The resulting filtrate were concentrated in vacuo to isolate 250 mg (yield: 85%) of 2b as colourless powder. To test the efficiency in large scale, the reaction was also performed for the mono-bromination of 1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product was isolated in 87% yield.[1] The milling apparatus was stopped and small portion of the sample was collected from the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing. |
| 82% |
With N-Bromosuccinimide In neat (no solvent) at 20℃; for 1h; Milling; Green chemistry; regioselective reaction; |
General procedure for synthesis of 2,4-dibromo-1-methoxy-3,5-dimethylbenzene(2b) in ball-milling.
General procedure: 1-Methoxy-3,5-dimethylbenzene (100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reactionwas monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetateand cooled at 0 °C. The product was isolated as filtrate upon paper filtrationand waste succinimide as precipitate. The resulting filtrate were concentrated in vacuoto isolate 250 mg (yield: 85%) of 2bas colourless powder. To test the efficiency in largescale, the reaction was also performed for the mono-bromination of1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product wasisolated in 87% yield.[1] Themilling apparatus was stopped and small portion of the sample was collectedfrom the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing. |
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With chloroform; bromine |
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With bromine In chloroform; toluene |
29 1-Bromo-2,4-dimethoxy-5-nitro-benzene
EXAMPLE 29 (METHOD 7C) 1-Bromo-2,4-dimethoxy-5-nitro-benzene To a solution of 2,4-dimethoxy-nitrobenzene (0.50 g) in chloroform (3 mL) is added dropwise a solution of bromine (0.23 g) in chloroform (1 mL) and the mixture is allowed to stir at room temperature for approximately 15 hours. Additional bromine (0.15 g) in chloroform (1 mL) is added and the reaction is stirred for an additional 4 hours. The mixture is then poured onto 5% aqueous sodium bisulfite and then extracted with chloroform. Pooled organic extracts are then washed successively with 5% aqueous sodium bisulfite then saturated sodium chloride, and then dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure and recrystallization of the residue from toluene provides the desired product as a yellow solid. |
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With bromine In chloroform at 20℃; for 29h; |
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With bromine In chloroform at 20℃; for 19h; |
29.7C EXAMPLE 29 (METHOD 7C); 1-Bromo-2,4-dimethoxy-5-nitro-benzene
To a solution of 2,4-dimethoxy-nitrobenzene (0.50 g) in chloroform (3 mL) is added dropwise a solution of bromine (0.23 g) in chloroform (1 mL) and the mixture is allowed to stir at room temperature for approximately 15 hours. Additional bromine (0.15 g) in chloroform (1 mL) is added and the reaction is stirred for an additional 4 hours. The mixture is then poured onto 5% aqueous sodium bisulfite and then extracted with chloroform. Pooled organic extracts are then washed successively with 5% aqueous sodium bisulfite then saturated sodium chloride, and then dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure and recrystallization of the residue from toluene provides the desired product as a yellow solid. |
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With bromine In chloroform at 0 - 20℃; for 4h; |
17
1,3-Dimethoxy-4-nitrobenzene (5.0 g, 27 mmol) in chloroform (50 ml) at 0°C, was treated with a solution of bromine (1.68 ml, 33 mmol) in chloroform (50 ml). The solution was stirred with warming to room temperature for 4 hours, washed with 10% sodium thiosulfate solution and brine then dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product was used without further purification(D17). MS (ES+) m/e 262/264 [M+H]+. |
Reference：
[1]Zornik, Denise; Meudtner, Robert M.; Ela Malah, Tamer; Thiele, Christina M.; Hecht, Stefan
[Chemistry - A European Journal, 2011, vol. 17, # 5, p. 1473 - 1484]
[2]Bose, Anima; Mal, Prasenjit
[Tetrahedron Letters, 2014, vol. 55, # 13, p. 2154 - 2156]
[3]Bose, Anima; Mal, Prasenjit
[Tetrahedron Letters, 2015, vol. 55, # 13, p. 2154 - 2156]
[4]Kaneniwa
[Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 785][Yakugaku Zasshi, 1955, vol. 75, p. 791,794][Chem.Abstr., 1956, p. 4842]
[5]Current Patent Assignee: PFIZER INC - US6166028, 2000, A
[6]Current Patent Assignee: PFIZER INC - US6335350, 2002, B1
Location in patent: Example 29
[7]Current Patent Assignee: PFIZER INC - EP1137645, 2004, B1
Location in patent: Page 31
[8]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/10629, 2006, A1
Location in patent: Page/Page column 49
- 2
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[ 3163-07-3 ]
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[ 778599-56-7 ]
- 3
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[ 16292-95-8 ]
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[ 778599-56-7 ]
- 4
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[ 704-14-3 ]
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[ 778599-56-7 ]
- 5
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[ 345-24-4 ]
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[ 124-41-4 ]
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[ 778599-56-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
In 1,4-dioxane; for 24h;Heating / reflux; |
A mixture of <strong>[345-24-4]1-bromo-2,4-difluoro-5-nitrobenzene</strong> (0.010 mol) and NaOMe (0.05Q mol) indioxane (20 mL) is stirred and under reflux conditions for 24 h. After being cooled to roomtemperature, the reaction mixture is poured into water and extracted with EtOAc. The separatedorganic layer is washed with brine, dried over MgS04 and evaporated in vacuo to give 1-bromo-2,4-dimethoxy-5-nitrobenzene as brown solids.Rf: 0.50 (hexane:EtOAc=1:1). 1H NMR (CDCI3) 5 3.999 (s, 3H), 4.001 (s, 3H), 6.52 (s, 1H), 8.25(s,1H) |
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