Benzoyl Peroxide → 6-Acetyl-3-(bromomethyl)-4-chloro-3'-fluorobiphenyl-2-carbonitrile

HRID 1192589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192589
[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH3:19])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH2:19][Br:21])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

Produkt 1

HCID 583686246-Acetyl-3-(bromomethyl)-4-chloro-3'-fluorobiphenyl-2-carbonitrileAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-carbonitrile (1.00 g, 3.48 mmol), N-bromosuccinimide (0.650 g, 3.65 mmol), and benzoyl peroxide (0.0421 g, 0.174 mmol) in carbon tetrachloride (10 mL) was heated at reflux overnight. After cooling to room temperature, the mixture was diluted with dichloromethane and washed with water. The organic layers were dried over magnesium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to give the desired product (0.57 g, 45%). LCMS calculated for C16H11BrClFNO (M+H)+: m/z=366.0; Found: 366.0.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with water
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-41a08f3671cd43adab0aa1e4eb33e566
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680108B2

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