Potassium Carbonate → 4-Bromo-3,5-dimethylphenyl 3-(4-nitrophenyl)propiolate
Reaktionsgleichung
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([CH3:30])[CH:23]=1)(=[O:20])[C:18]#[CH:19]>C1COCC1.[Cu]I>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:19]#[C:18][C:17]([O:21][C:22]2[CH:23]=[C:24]([CH3:30])[C:25]([Br:29])=[C:26]([CH3:28])[CH:27]=2)=[O:20])=[CH:3][CH:4]=1)([O-:10])=[O:9]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
1-Iodo-4-nitrobenzene (550 mg, 2.17 mmol) in THF (4 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (552 mg, 298.6 mmol), CuI (30 mg, 0.16 mmol) and PdCl2(Ph3P)2 (14 mg, 0.020 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (506 mg, 2.03 mmol) in THF (2.5 mL) was added by syringe pump over a period of 6 h. After being cooled to room temperature, the mixture was filtered and washed with EtOAc. The filtrate was concentrated and purified by silica gel column chromatography to give the title compound 7-1 (551 mg, 74% yield) as a brown solid.
Aufarbeitung
- additionnitrogen gas was introduced
- temperatureAfter being cooled to room temperature
- filtrationthe mixture was filtered
- washwashed with EtOAc
- concentrationThe filtrate was concentrated
- custompurified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-cb9e5fa46bd34dd29ce6afa7a9084312
- Quelldatensatz
- uspto-grants-2016_08
- Patentnummer
- US09416121B2
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