Hydrochloric Acid → (4-Bromophenyl)(4-hydroxyphenyl)methanone

HRID 229126

Reaktionsgleichung

Reaktionsgleichung von HRID 229126
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].N#N.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 7943334-Bromo-4'-methoxybenzophenoneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 4570728(4-Bromophenyl)(4-hydroxyphenyl)methanoneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of (4-bromophenyl)[4-(methyloxy)phenyl]methanone (1) (27.0 g, 0.93 mol) in toluene (400 mL) was slowly added AlCl3 (32.0 g, 0.23 mol, 2.5 eq) via a powder addition funnel under a nitrogen atmosphere at RT. The stirred reaction mixture was heated at reflux for 5 h under a blanket of N2. The reaction mixture was allowed to cool to RT and then poured into 10% aqueous HCl (1 L). The reaction mixture was transferred to a separatory funnel and the layers were separated. The aqueous phase was extracted with EtOAc (4×250 mL). The combined organic layer was washed with brine (2×100 mL), dried (Na2SO4), and filtered. The filtrate was concentrated under reduced pressure to afford 25.75 g (100%) of compound 2 as a tan solid that was used in subsequent reactions without any further purification. 1H NMR (300 MHz, DMSO-d6): δ 6.89 (d, J=8.7 Hz, 2H), 7.60 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.7 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 10.48 (s, 1H).

Aufarbeitung

  1. additionvia a powder addition funnel under a nitrogen atmosphere at RT
  2. customThe stirred reaction mixture
  3. temperaturewas heated
  4. customThe reaction mixture was transferred to a separatory funnel
  5. customthe layers were separated
  6. extractionThe aqueous phase was extracted with EtOAc (4×250 mL)
  7. washThe combined organic layer was washed with brine (2×100 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2c3fe2771ee0470e82f8de0e79166af7
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560589B2

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