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

HRID 369557

Reaktionsgleichung

Reaktionsgleichung von HRID 369557
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>O>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:14])=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10008Fluorobenzene2×HCID 685154-Bromobenzoyl chloride2×HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 74951(4-Bromophenyl)(4-fluorophenyl)methanoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-bromo-4'-fluorobenzophenone was synthesized by the Friedel-Crafts acylation of fluorobenzene with 4-bromobenzoyl chloride. More specifically, fluorobenzene (117 grams, 1.2 mol) and 4-bromobenzoyl chloride (39.8 grams, 0.18 mol) was charged to a 250 milliliter flask equipped with a mechanical stirrer, N2 inlet, and reflux condenser. The mixture was then cooled to 0° C. and anhydrous AlCl3 (27 grams, 0.20 mol) was added. The mixture was stirred for 15 minutes at 23° C. for 16 hours. The resulting slurry was poured into 2 liters of water acidified with HCl. The organics were extracted with methylene chloride and subsequently dried over MgSO4. The slurry was filtered and the methylene chloride was removed under reduced pressure. Recrystallization from ethanol gave 43.4 grams (86 percent yield) of the desired crystalline product.

Aufarbeitung

  1. customequipped with a mechanical stirrer, N2 inlet
  2. temperaturereflux condenser
  3. extractionThe organics were extracted with methylene chloride
  4. dry with materialsubsequently dried over MgSO4
  5. filtrationThe slurry was filtered
  6. customthe methylene chloride was removed under reduced pressure
  7. customRecrystallization from ethanol
  8. customgave 43.4 grams (86 percent yield) of the desired crystalline product

Quellen und Nachweise

ORD-Eintrag
ord-d677a949b91b48b8b188e07abe3b747b
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06139920

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