N-bromobutanimide → 2-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene

HRID 1874912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874912
[Br:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([Cl:18])=[C:6]([O:8][C:9]2[C:14]([F:15])=[C:13]([CH3:16])[CH:12]=[CH:11][C:10]=2[Cl:17])[CH:7]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([Cl:18])=[C:6]([O:8][C:9]2[C:14]([F:15])=[C:13]([CH2:16][Br:27])[CH:12]=[CH:11][C:10]=2[Cl:17])[CH:7]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 684864972-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene

Produkt 1

HCID 866448922-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzeneAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (13.25 g, 36.0 mmol) and NBS (6.41 g, 36.0 mmol) were combined in carbon tetrachloride (150 mL) with a catalytic amount of AIBN (0.296 g, 1.800 mmol) and stirred at reflux for 16 h. The reaction mixture was washed with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by chromatography on 330 g silica gel eluted with 0 to 10% Et2O in hexanes to give the desired product, 2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (10.04 g, 22.47 mmol, 62.4% yield), as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.53-7.67 (m, 3H), 6.78 (s, 1H), 4.75 (s, 2H).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography on 330 g silica gel
  7. washeluted with 0 to 10% Et2O in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ca351a5edb2b4d23aa0aa46920519ffa
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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