Benzene, 1-bromo-4-(trifluoromethyl)- → Methanone, (3-methoxyphenyl)[4-(trifluoromethyl)phenyl]-

HRID 614699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614699
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([O-])=[O:23].[Na+]>CCOCC.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[C:19]([O:18][CH3:17])[CH:20]=2)=[CH:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-2×HCID 23719438Sodium 3-methoxybenzoateHCID 178418339Butyllithium

Produkt 1

HCID 12139417Methanone, (3-methoxyphenyl)[4-(trifluoromethyl)phenyl]-Ausbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

This is carried out under nitrogen at -60° C. 0.29 mol (65 g) of para-bromo-trifluoromethylbenzene dissolved in 100 ml of anhydrous ether is added dropwise to 0.29 mol of butyl-lithium in solution in ether (1.48 mol/liter). The reaction is followed by gas phase chromatography; when there is no longer any remaining para-bromo-trifluoromethylbenzene, 0.29 mol (50.5 g) of sodium 3-methoxybenzoate is added. The mixture is allowed to return to ambient temperature. After stirring for 64 hours, it is hydrolysed in iced water. The batch is extracted with ether. The ether phase is dried, decolorised and concentrated. 45 g of a product which has been recrystallised from a mixture of isopropyl ether and hexane are obtained. Melting point 69° C. Yield: 55%.

Aufarbeitung

  1. customThis is carried out under nitrogen at -60° C
  2. additionis added
  3. customto return to ambient temperature
  4. extractionThe batch is extracted with ether
  5. dry with materialThe ether phase is dried
  6. concentrationconcentrated
  7. custom45 g of a product which has been recrystallised from a mixture of isopropyl ether and hexane
  8. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-c5ef19d9d98d4d0d92d89040b15345d5
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04146385

Notizen zur Reaktion

Wird geladen…