Potassium Carbonate → 1,3-Bis(trifluoromethyl)-5-(1,1,1-trifluoroprop-2-en-2-yl)benzene
Reaktionsgleichung
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:19]([C:21]([F:24])([F:23])[F:22])=[CH2:20].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:19]([C:21]([F:24])([F:23])[F:22])=[CH2:20])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A mixture of 3,5-bis(trifluoromethyl)phenylboronic acid (2.2 g, 8.5 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (1.79 g, 10.2 mmol), Pd(PPh3)2Cl2(179 mg, 0.26 mmol), K2CO3 (2.35 g, 17 mmol), and Cu2O (37 mg, 0.26 mmol) in THF (6 mL) and H2O (3 mL) in a tube sealed under N2 was heated at 80° C. for 4 h, cooled to rt and partitioned between EA and water, extracted with EA (3×20 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE to afford 1,3-bis(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.5 g, yield 55%) as oil.
Aufarbeitung
- customsealed under N2
- temperaturecooled to rt
- custompartitioned between EA and water
- extractionextracted with EA (3×20 mL)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography over silica gel
- washeluted with PE
Quellen und Nachweise
- ORD-Eintrag
- ord-d48e37e87b1b4574a9d4f733aff64403
- Quelldatensatz
- uspto-grants-2014_10
- Patentnummer
- US08853186B2
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