Azobisisobutyronitrile → Ethyl 2-(bromomethyl)-3,6-dichlorobenzoate

HRID 577498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577498
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([C:10]([Cl:13])=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl.ClCCl>[Br:15][CH2:14][C:3]1[C:2]([Cl:1])=[CH:12][CH:11]=[C:10]([Cl:13])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 86723723Ethyl 3,6-dichloro-2-methylbenzoate

Produkt 1

HCID 86723724Ethyl 2-(bromomethyl)-3,6-dichlorobenzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3,6-dichloro-2-methylbenzoate (253b, 120 g, 0.52 mol) and N-bromosuccinimide (147 g, 0.82 mol) in chloroform (1 L) was treated with azobisisobutyronitrile (25.3 g, 0.15 mol) and the mixture refluxed overnight. After cooling to room temperature, the mixture was diluted with dichloromethane (800 mL) and washed with water (1.2 L). The aqueous layer was extracted with dichloromethane (800 mL). The combined organic extracts were washed with saturated aqueous sodium chloride solution (1.5 L), dried over sodium sulfate, and concentrated in vacuo to give ethyl 2-(bromomethyl)-3,6-dichlorobenzoate (253c, 160 g, 100% yield) which was used without further purification.

Aufarbeitung

  1. temperaturethe mixture refluxed overnight
  2. washwashed with water (1.2 L)
  3. extractionThe aqueous layer was extracted with dichloromethane (800 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution (1.5 L)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3d86e46f619942e29e00f8256a694502
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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