Benzyl Bromide → Dibenzyl-(4-iodo-2,5-dimethylphenyl)amine

HRID 1039837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039837
[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:11]([N:4]([CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=1)[C:3]1[CH:5]=[C:6]([CH3:10])[C:7]([I:9])=[CH:8][C:2]=1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

Produkt 1

HCID 57461072Dibenzyl-(4-iodo-2,5-dimethylphenyl)amineAusbeute 167,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2,5-dimethyl-4-iodoaniline (6.44 g, 26.1 mmol), benzyl bromide (11.50 g, 67.24 mmol) and potassium carbonate (8.20 g, 59.3 mmol) in EtOH (100 mL) was stirred at 50° C. for 12 h. The reaction mixture was then concentrated under reduced pressure. The residue (a purple solid) was mixed with DCM and this mixture was filtered using vacuum. The filtrate was purified by silica gel flash chromatography (0-5% MeOH in DCM) to give the title compound (9.35 g, 83% yield) as an oil.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionThe residue (a purple solid) was mixed with DCM
  3. filtrationthis mixture was filtered
  4. customThe filtrate was purified by silica gel flash chromatography (0-5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-26f8f7091e9848f0ade7da0d1cdc41d8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551978B2

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