Azobisisobutyronitrile → 4-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile

HRID 1875210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875210
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[F:17])=[C:6]([F:18])[C:5]([CH3:19])=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:19][C:5]1[C:6]([F:18])=[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[F:17])[C:2]([Cl:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 687209894-[(6-Chloro-2-fluoro-3-methylphenyl)oxy]-3-fluorobenzonitrile

Produkt 1

HCID 687226214-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrileAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-3-fluorobenzonitrile (2.41 g, 8.62 mmol) and NBS (1.534 g, 8.62 mmol) in carbon tetrachloride (150 ml) was added AIBN (1.415 g, 8.62 mmol) and the reaction mixture was stirred at 80° C. overnight. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile (1.60 g, 4.46 mmol, 52% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (dd, 1H), 7.62 (d, 1H), 7.48-7.59 (m, 2H), 6.92 (t, 1H), 4.70 (s, 2H).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe crude material was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-239265706bd24a09b1a3b27b29ac51d4
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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