N-bromobutanimide → 1-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene

HRID 644957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644957
[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH2:13][Br:15])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:4])[F:5]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 74438Benzene, 1-methyl-3-(1,1,2,2-tetrafluoroethoxy)-

Produkt 1

HCID 114603781-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzeneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

EX-1A) To a solution of 3-(1,1,2,2-tetrafluoroethoxy)toluene (50 g, 0.24 mol) and N-bromosuccinimide (42.75 g, 0.24 mol) in 100 mL of carbon tetrachloride under nitrogen was added 2,2′-azobisisobutyronitrile (0.71 g, 0.004 mol). The resultant mixture was refluxed for 2 h, then cooled to room temperature and quenched with 300 mL of water. The organic layer was collected, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give 66.0 g (96%) of the desired crude 3-(1,1,2,2-tetrafluoroethoxy)bromomethylbenzene product as a yellow oil. 1H NMR indicates that this oil is a mixture of products: 7% dibrominated, 67% monobrominated, and 20% starting material. The crude product was used without further purification. ESMS m/z=287 [M+H]+.

Aufarbeitung

  1. customquenched with 300 mL of water
  2. customThe organic layer was collected
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0dcc3ca9b4eb47b091f1a3f8fbbd08b8
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700658B2

Notizen zur Reaktion

Wird geladen…