Hydrochloric Acid → 4-Bromo-4'-methoxybenzophenone

HRID 229125

Reaktionsgleichung

Reaktionsgleichung von HRID 229125
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:14]2[CH:15]=[CH:16][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 7943334-Bromo-4'-methoxybenzophenoneAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cooled (ice bath, 5° C.) mixture of 4-bromobenzoyl chloride (25.0 g, 0.114 mol) and anisole (15.5 g, 0.143 mol, 1.25 eq) in CH2Cl2 (500 mL) was added AlCl3 (19.0 g, 0.143 mol, 1.25 eq) portion-wise over a period of 20 minutes with stirring under a nitrogen atmosphere. The resulting reaction mixture was allowed to stir between 5° C. and 20° C. for 3 h. The reaction mixture was poured slowly into 20% aqueous HCl (500 mL), stirred for 15 min, and layers were separated. The aqueous layer was further extracted with CH2Cl2 (3×250 mL). The combined organic layer was washed with water (200 mL), brine (200 mL) dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 33.48 g (100%) of compound 1 as a white solid. 1H NMR (300 MHz, CDCl3): δ 3.91 (s, 3H), 6.99 (d, J=8.7 Hz, 2H), 7.65 (s, 4H), 7.82 (d, J=8.7 Hz, 2H).

Aufarbeitung

  1. temperatureTo a cooled
  2. customThe resulting reaction mixture
  3. stirringto stir between 5° C. and 20° C. for 3 h
  4. stirringstirred for 15 min
  5. customlayers were separated
  6. extractionThe aqueous layer was further extracted with CH2Cl2 (3×250 mL)
  7. washThe combined organic layer was washed with water (200 mL), brine (200 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b5dd5c6d5383494cb8c90b2123ce6d94
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560589B2

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