Reaktionsgleichung
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[OH:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][C:27](O)=[CH:28][CH:29]=2)[CH:24]=1>CC#N>[Br:20][C:27]1[CH:26]=[C:25]2[C:30]([CH:31]=[CH:32][C:23]([OH:22])=[CH:24]2)=[CH:29][CH:28]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 10 °C
Versuchsvorschrift
Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10° C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280° C. over 30 minutes giving a black liquid. The liquid was heated to 310° C. over 20 minutes and the temperature was maintained at 310° C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87% pure by HPLC (43% yield).
Aufarbeitung
- customThe cooling bath was removed
- washrinse
- temperatureThe resulting yellow tan mixture was heated
- temperatureat reflux for 3 hours
- distillationAcetonitrile was distilled off
- customresulting in a grayish white solid
- temperatureThe solid was heated to 280° C. over 30 minutes
- customgiving a black liquid
- temperatureThe liquid was heated to 310° C. over 20 minutes
- temperaturethe temperature was maintained at 310° C. for an additional 15 minutes until gas evolution
- temperatureThe black mixture was cooled to room temperature
Quellen und Nachweise
- ORD-Eintrag
- ord-573ac339c38149fe8cf5990f4a3211f8
- Quelldatensatz
- uspto-grants-2005_01
- Patentnummer
- US06844344B2
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