t-Butyl bromide → Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

HRID 2191624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191624
CN(C)C(=O)C.[F:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][C:13]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:34]([CH3:37])([CH3:36])[CH3:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[F:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][C:13]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=2[C:15]([O:17][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:16])=[CH:10][CH:9]=1

Komponenten

8

Edukt 4

HCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 576678972-(4-Fluoroanilino)-4-nitrobenzoic acid

Produkt 1

HCID 68965268Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To N,N-dimethylacetamide 15 mL solution of 2-(4-fluoroanilino)-4-nitrobenzoic acid 1.0 g, were added potassium carbonate 9.9 g, benzyltriethylammonium chloride 0.82 g and 2-bromo-2-methylpropane 21 mL at room temperature, and it was stirred at 55° C. for 4 hours. After the reaction mixture was cooled to room temperature,2-bromo-2-methylpropane 21 mL was added to it, and it was stirred at 55° C. for 12 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and 10% citric acid aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to give tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate 1.1 g of red oil.

Aufarbeitung

  1. additionwas added to it, and it
  2. stirringwas stirred at 55° C. for 12 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washafter sequential washing with water and 10% citric acid aqueous solution
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06b2e4c2d8d74843ace974954c3728ae
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08327467B2

Notizen zur Reaktion

Wird geladen…