Azobisisobutyronitrile → 3-bromo-4-(bromomethyl)benzoic Acid

HRID 594068

Reaktionsgleichung

Reaktionsgleichung von HRID 594068
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:31])C(=O)C1>FC(F)(F)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][Br:31])[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 821303-Bromo-4-methylbenzoic acid

Produkt 1

HCID 116163143-bromo-4-(bromomethyl)benzoic AcidAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7368(Trifluoromethyl)benzeneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3-bromo-4-methylbenzoic acid (1.0 equiv.) and AIBN (0.05 equiv.) in trifluorotoluene (0.28 M) was added NBS (1.1 equiv.). The mixture was heated at 90° C. overnight. The reaction mixture was partitioned between EtOAc and H2O. The organic layer was washed with NaCl(sat.), dried over MgSO4, filtered, concentrated to yield 3-bromo-4-(bromomethyl)benzoic acid in 60% yield. LC/MS (m/z)=294.8 (MH+), Rt=0.80 min.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. washThe organic layer was washed with NaCl(sat.)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a5833216af294f4aa238714c4ebbf9dd
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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