4-(5-Fluoro-2-methoxyphenyl)-4-methylpentan-2-one → 1-Bromo-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one

HRID 1061645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061645
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]([CH3:14])([CH3:13])[CH2:9][C:10](=[O:12])[CH3:11])[CH:7]=1.[Br-:17].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl.CO>[Br:17][CH2:11][C:10](=[O:12])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:15][CH3:16])([CH3:13])[CH3:14]

Komponenten

5

Edukt 2

HCID 222849224-(5-Fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 53442637Benzyltrimethylammoniumtribromide

Produkt 1

HCID 222849461-Bromo-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of the above ketone (1.34 g, 6 mmol) in methylene chloride (35 mL) and MeOH (5 mL), benzyltrimethylammonium tribromide (2.57 g, 6.6 mmol) was added at ambient temperature. After 30 minutes, TLC (hexanes-EtOAc (9:1)) showed complete disappearance of the starting material. The reaction mixture was diluted with methylene chloride (50 mL), washed with two 50 mL portions of water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 1-bromo-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one as a light brown liquid (80%) which was used for the next reaction without further purification.

Aufarbeitung

  1. washwashed with two 50 mL portions of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6775a5fb302045439408e6cd6aaa24c2
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960581B2

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