1-Bromopentane → 4-Bromo-3-chloro-N,N-dipentylaniline

HRID 1250004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250004
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[Cl:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:2]([N:12]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:11]1[CH:13]=[CH:14][C:8]([Br:7])=[C:9]([Cl:15])[CH:10]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 888884-Bromo-3-chloroaniline

Produkt 1

HCID 183293124-Bromo-3-chloro-N,N-dipentylanilineAusbeute 106,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Bromopentane (0.42 mL, 3.4 mmol) was added to a mixture of 4-bromo-3-chloroaniline (200 mg, 0.9 mmol) and potassium carbonate (199 mg, 1.4 mmol) in DMF (20 mL) and the reaction was heated to 13 0˜˜C overnight. The mixture was cooled, diluted with water (20 mL) and extracted with petroleum ether (3×25mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography using 9:1 petroleum ether:ethyl acetate as eluent to give N,N-Dipentyl-4-bromo-3-chloroaniline (1) (332 mg, 68%). 1HNMR (CDCI3) 67.02 (d, IH, ArH); 3.12 (t, 4H, 2×NCH2); 0.95 (t, 6H, 2×CH3). MS; 347 (M+H).

Aufarbeitung

  1. temperaturethe reaction was heated to 13 0˜˜C overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted with petroleum ether (3×25mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d25a5bcc6d6e468e9ad3ba3787307468
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335446B1

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