Methylamine → 5-Bromo-3-fluoro-N-methyl-2-nitroaniline

HRID 59932

Reaktionsgleichung

Reaktionsgleichung von HRID 59932
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[C:6]([F:14])[C:7]([N+:11]([O-:13])=[O:12])=[C:8](F)[CH:9]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([F:14])[C:7]([N+:11]([O-:13])=[O:12])=[C:8]([NH:2][CH3:1])[CH:9]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 10796Cesium carbonateHCID 213354875-Bromo-1,3-difluoro-2-nitrobenzene

Produkt 1

HCID 716520385-Bromo-3-fluoro-N-methyl-2-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2 M MeNH2 in THF (82 mL) was added dropwise to a solution of 5-bromo-1,3-difluoro-2-nitrobenzene (164 mmol) and Cs2CO3 (197 mmol) in THF (1 L). The reaction mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc and H2O. The two phases were separated and the organic layer was dried (Na2SO4) and concentrated to afford the desired product.

Aufarbeitung

  1. waitat room temperature for 1 h
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was partitioned between EtOAc and H2O
  4. customThe two phases were separated
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dbfc8f0c4dbe4079969af08fe4403998
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440929B2

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