4-Chloro-4'-isopropylbutyrophenone → 1-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

HRID 1018073

Reaktionsgleichung

Reaktionsgleichung von HRID 1018073
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:6].[Br:16]([O-])(=O)=O.[Na+].[Br-].[Na+]>C(Cl)Cl.O.S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>[Br:16][C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])=[CH:12][CH:11]=1)([CH3:15])[CH3:14]

Komponenten

7

Edukt 3

HCID 987444-Chloro-4'-isopropylbutyrophenoneHCID 253881Sodium BromideHCID 23668195Sodium Bromate

Produkt 1

HCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-Ausbeute 281,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 146045Sodium dithionateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (74.7 g, 333 mmol) in methylene chloride (250 mL) and add sodium bromate (17.6 g, 117 mmol) in water (75 mL) in a three-necked Morton flask equipped with an overhead stirrer. Cool the solution to 10° C. and irradiate with two 150 W incandescent flood lamps. Add, by dropwise addition, a solution of sodium bromide (24 g, 233 mmol) and stir for 2 hours. Illuminate for another 30 minutes, add sodium dithionate (2.0 g), separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (100 g, 99%).

Aufarbeitung

  1. customequipped with an overhead stirrer
  2. customirradiate with two 150 W incandescent flood lamps
  3. additionAdd, by dropwise addition
  4. customIlluminate for another 30 minutes
  5. customseparate the organic phase
  6. dry with materialdry (MgSO4)
  7. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b2b8f69c1a0413696162a20122ef69b
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479663B2

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