Reaktionsgleichung
Br[C:2]1[S:3][C:4]([Cl:7])=[CH:5][CH:6]=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:7][C:4]1[S:3][C:2]([C:9]2[S:8][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1Komponenten
Versuchsvorschrift
To a solution of 2-bromo-5-chlorothiophene (4.11 g), thiophene-2-boronic acid (4.00 g), tetrakis(triphenylphosphine)palladium (0) (1.20 g) and 2M aqueous sodium carbonate solution (31.3 ml) in dimethoxyethane (100 ml) was heated under reflux under argon atmosphere for 2.5 hours. The reaction mixture was cooled, and extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give 2-(5-chloro-2-thienyl) thiophene (3.37 g) as pale yellow oil. (2) The above 2-(5-chloro-2-thienyl)thiophene and 5-bromo-2-methylbenzoic acid obtained in Reference Example 4-(1) were used and treated in a manner similar to Reference Example 5 to give 5-bromo-1-(5-(5-chloro-2-thienyl)-2-thienylmethyl)-2-methylbenzene as a colorless solid. APCI-Mass m/Z 383/385 (M+H).
Aufarbeitung
- temperatureunder reflux under argon atmosphere for 2.5 hours
- temperatureThe reaction mixture was cooled
- extractionextracted with ethyl acetate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-42a2dc9ff65b42988b17141fa24ff97e
- Quelldatensatz
- uspto-grants-2012_06
- Patentnummer
- US08202984B2
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