1,2-Dichloroethane → 2-Bromo-N-methoxy-N,5-dimethylbenzamide

HRID 501712

Reaktionsgleichung

Reaktionsgleichung von HRID 501712
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2280802-Bromo-5-methylbenzoic acid

Produkt 1

HCID 534166972-Bromo-N-methoxy-N,5-dimethylbenzamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Step AI (1): To a solution of 2-bromo-5-methylbenzoic acid (1000.0 mg, 4.65 mmol) in DMF (100 mL) were added N,O-dimethylhydroxylamine hydrochloride (454 mg, 4.65 mmol), EDC (891 mg, 4.65 mmol), and HOBT (628 mg, 4.65 mmol). The reaction mixture was stirred at rt for 2.5 days. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give 2-bromo-N-methoxy-N,5-dimethylbenzamide (656 mg, 55%) as a colorless oil. LC-MS (M+H)+=258.21.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8650cec7e005429a8345bcad56f16495
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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