Alternatived Products of [ 59862-83-8 ]
Product Details of [ 59862-83-8 ]
| CAS No. : | 59862-83-8 |
MDL No. : | MFCD06657484 |
| Formula : |
C9H11BrO3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | JFDAPDWITQSTRY-UHFFFAOYSA-N |
| M.W : | 247.09 |
Pubchem ID : | 18788676 |
| Synonyms : |
|
Application In Synthesis of [ 59862-83-8 ]
* 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 [ 59862-83-8 ]
- 1
-
[ 32460-00-7 ]
-
[ 24424-99-5 ]
-
[ 59862-83-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 84% |
Stage #1: 2,5-dibromofuran With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃;
Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃;
Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.; |
|
| 84% |
Stage #1: 2,5-dibromofuran With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 1h; Inert atmosphere;
Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; for 2h; Inert atmosphere; |
|
Reference：
[1]Li, Hongmei; Balsells, Jaume
[Tetrahedron Letters, 2008, vol. 49, # 12, p. 2034 - 2037]
[2]Arredondo, Juan D.; Li, Hongmei; Balsells, Jaume
[Organic Syntheses, 2012, vol. 89, p. 460 - 470]
- 2
-
[ 214210-21-6 ]
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[ 59862-83-8 ]
-
[ 945468-34-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 53% |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In monoethylene glycol diethyl ether; water; at 90℃; for 24h; |
EXAMPLE 2; 2.1 tert-Butyl 5-(3-cyano-4-fluorophenyl)furan-2-carboxylate12.9 g of <strong>[214210-21-6]4-fluoro-3-cyanobenzeneboronic acid</strong>, 14.8 g of tert-butyl 5-bromofuran-2-carboxylate, 30.0 g of sodium hydrogencarbonate, 2.0 g of tetrakis(triphenylphosphine)palladium(0), 300 ml of ethylene glycol dimethyl ether and 200 ml of water are degassed a number of times and blanketed with nitrogen. The reaction mixture is stirred at a bath temperature of 90 C. under nitrogen for 24 hours. After cooling, the mixture is treated with water and ethyl acetate, and the phases are separated. The aqueous phase is extracted a number of times with ethyl acetate, the combined organic phases are dried and evaporated to dryness. The residue is treated firstly with PE, subsequently with a little EA and filtered off with suction (K1). The EA mother liquor is evaporated, and the residue is recrystallised from a little EA (K2) After drying, combination of K1 and K2 gives 11.8 g of tert-butyl 5-(3-cyano-4-fluorophenyl)furan-2-carboxylate (53%) as virtually colourless powder. |
| 53% |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 24h; |
2.1 Preparation of tert-butyl 5-(3-cyano-4-fluorophenyl)furan-2-carboxylate (?A10?)12.9 g of <strong>[214210-21-6]4-fluoro-3-cyanobenzeneboronic acid</strong>, 14.8 g of tert-butyl 5-bromofuran-2-carboxylate, 30.0 g of sodium hydrogencarbonate, 2.0 g of tetrakis(triphenylphosphine)palladium(0), 300 ml of ethylene glycol dimethyl ether and 200 ml of water are degassed a number of times and blanketed with nitrogen. The reaction mixture is stirred at a bath temperature of 90 C. under nitrogen for 24 hours. After cooling, the mixture is treated with water and ethyl acetate, and the phases are separated. The aqueous phase is then extracted with ethyl acetate a number of times, the combined organic phases are dried and evaporated to dryness. The residue is treated firstly with petroleum ether, subsequently with a little ethyl acetate (EA) and filtered off with suction (K1). The EA mother liquor is evaporated, and the residue is recrystallised from a little EA (K2). After drying, combination of K1 and K2 gives 11.8 g of tert-butyl 5-(3-cyano-4-fluorophenyl)furan-2-carboxylate (53%) as a virtually colourless powder. |
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