Water → N-Allyl-N-(4-fluorophenyl)amine

HRID 1676352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676352
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][CH:11]=[CH2:12].C([O-])([O-])=O.[K+].[K+].O>C1COCC1.CCOC(C)=O>[CH2:12]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:11]=[CH2:10]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7841Allyl bromideHCID 97314-FluoroanilineHCID 11430Potassium Carbonate

Produkt 1

HCID 11829634N-Allyl-N-(4-fluorophenyl)amineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 4-fluorobenzenamine (25 g, 225 mmol), 3-bromoprop-1-ene (19.0 ml, 225 mmol) and K2CO3 (31.1 g, 225 mmol) was stirred in THF (1 L) for 2 days. Water (20 mL) and EtOAc (1 L) were added into the reaction mixture. The organics was separated and washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (20% EtOAc in hexane) to afford the product (16 g, 47.0% yield) as orange brown oil. 1H NMR (400 MHz, CDCl3): δ 6.85-6.90 (m, 2H), 6.53-6.60 (m, 2H), 5.89-6.01 (m, 1H), 5.25-5.32 (m, 1H), 5.15-5.20 (m, 1H), 3.71-3.77 (m, 2H), 3.66 (br s, 1H).

Aufarbeitung

  1. customThe organics was separated
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7d114cd5da3e48819d008acb8c5fb401
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003662B2

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