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Trifluoroacetic acid → 4-Bromo-3-methyl-5-nitroaniline

HRID 723099
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 723099
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([Br:17])=[C:10]([CH3:18])[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[Br:17][C:11]1[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=1[CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69586631(4-Bromo-3-methyl-5-nitro-phenyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 218864724-Bromo-3-methyl-5-nitroanilineAusbeute 112,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(4-Bromo-3-methyl-5-nitro-phenyl)-carbamic acid tert-butyl ester (1000 mg, 2.9 mmol) was dissolved into DCM (10 mL). To this was added TFA (10 mL) and the reaction was stirred at RT for 1 hour. The pH was adjusted to 8 with 1 N NaOH and the solvents were removed in vacuo. The reaction mixture was dissolved into EtOAc and the layers were separated. The organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in title compound (756 mg, quantitative) as a brown oil. 1H-NMR (CDCl3): δ 8.44 (s, 1H), 8.02 (s, 1H), 7.61 (s, 1H), 3.05 (s, 3H).

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. dissolutionThe reaction mixture was dissolved into EtOAc
  3. customthe layers were separated
  4. dry with materialThe organic layers were dried (MgSO4)
  5. customthe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b83aeb6286434958bc03e83aef2b1156
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07138530B2

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