2-Bromopropane → Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-

HRID 263381

Reaktionsgleichung

Reaktionsgleichung von HRID 263381
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.Br[CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>>[Cl:9][C:5]1[C:6]([O:8][CH:12]([CH3:14])[CH3:13])=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1

Komponenten

4

Edukt 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 1586545-Amino-2-chloro-4-fluorophenol

Produkt 1

HCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-Ausbeute 62 %

Versuchsvorschrift

A stirring mixture of 5-amino-2-chloro-4-fluorophenol (22.0 g, 136.19 mmol), 2-bromopropane (38.4 mL, 50.25 g, 408.57 mmol) and potassium carbonate (37.6 g, 273.0 mmol) was heated at reflux for 17 h. The reaction mixture was cooled and filtered. The filtrate was evaporated to dryness under reduced pressure. Flash chromatography yielded the title compound of Step A as a brown oil (17.2 g). 1H NMR (CDCl3): δ7.02 (d, 1H), 6.44 (d, 1H) 4.38 (q, 1H), 3.81 (br s,2H), 1.33 (d,6H). IR (cm-1): 3378.4, 3475.6.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 17 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e7557914f99c40acbe835f6180c02ff1
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643855

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