Pyridine → 2-Bromo-4-chloro-6-methylbenzenamine

HRID 855239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855239
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.N1C=CC=CC=1.[Br:16]Br>C(Cl)Cl>[Br:16][C:7]1[CH:8]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:9])[C:5]=1[NH2:6]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 72514-Chloro-2-toluidineHCID 24408Bromine

Produkt 1

HCID 205437542-Bromo-4-chloro-6-methylbenzenamineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.83 g (20 mmol) of 4-chloro-2-methyl aniline and 1.74 g (22 mmol) of pyridine were dissolved in 20 ml DCM. 3.20 g (20 mmol) of bromine were added dropwise under cooling. The reaction mixture was stirred for 2 h at rt. The solvent was removed and the residue was dissolved in diethyl ether. The organic layer was washed with water, dried over sodium sulfate, filtered and the solvent was evaporated. The crude product was purified by column chromatography (silica gel; diethyl ether/heptane 1:1) to yield 3.91 g (89%) of 2-bromo-4-chloro-6-methyl aniline as a light green solid. 1H NMR (CDCl3, 300 MHz): δ 7.30 (s, 1H), 6.99 (s, 1H), 4.04 (br s, 2H), 2.19 (s, 3H).

Aufarbeitung

  1. temperatureunder cooling
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe crude product was purified by column chromatography (silica gel; diethyl ether/heptane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-473342d8ef434eebbe2e8436db4fcc66
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

Notizen zur Reaktion

Wird geladen…