5-Bromo-4-chloro-2-fluoro-n-methyl-n-o-tolyl-benzamide → 5-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide

HRID 1848610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848610
[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5](F)=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8].[CH3:21][O:22][Na].CO>>[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([O:22][CH3:21])=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8]

Komponenten

3

Edukt 2

HCID 686027675-Bromo-4-chloro-2-fluoro-n-methyl-n-o-tolyl-benzamideHCID 178501943HCID 178501943, Verbindung

Produkt 1

HCID 686036055-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide

Versuchsvorschrift

A mixture of 5-bromo-4-chloro-2-fluoro-N-methyl-N-o-tolyl-benzamide (2.5 g, 7.0 mmol) was heated in MeONa/MeOH (20 mL, 25%) at 55° C. for 12 hrs, then was concentrated and partitioned between DCM and water. The organic layer was then separated, washed with 3N HCl, sat NaHCO3 and brine, dried over MgSO4, and concentrated. Purification by silica gel column chromatography eluting with ethyl acetate in hexanes (1/4) gave 5-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide (2.75 g). MS: 367.8 (M+H)+; tR=2.51 min (method 1).

Aufarbeitung

  1. concentrationwas concentrated
  2. custompartitioned between DCM and water
  3. customThe organic layer was then separated
  4. washwashed with 3N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification by silica gel column chromatography
  8. washeluting with ethyl acetate in hexanes (1/4)

Quellen und Nachweise

ORD-Eintrag
ord-924c7802649c4f8c9a7b37f8c7cf6ba0
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952161B2

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