Iodoethane → (4-Bromo-2-tert-butylphenyl)diethylamine

HRID 1261515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261515
[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[CH2:15](I)[CH3:16].[Cl-].[NH4+].O1CC[CH2:22][CH2:21]1>CS(C)=O>[Br:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]([CH2:15][CH3:16])[CH2:21][CH3:22])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

Komponenten

7

Edukt 5

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 119590004-bromo-2-tert-butylphenylamine

Produkt 1

HCID 66671963(4-Bromo-2-tert-butylphenyl)diethylamineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

6.9 g (0.17 mol) of sodium hydride are suspended in 200 mL of tetrahydrofuran. 13 g (57 mmol) of 4-bromo-2-tert-butylaniline are added, along with 200 mL of dimethyl sulfoxide, added slowly. The mixture turns blue and, after 30 minutes, 13 mL (0.17 mol) of ethyl iodide are added and the reaction medium, which has turned white, is stirred at room temperature for 13 hours. The reaction medium is then poured into saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is then washed twice with water. It is dried and then concentrated to dryness. The residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate). 14.8 g of (4-bromo-2-tert-butylphenyl)diethylamine are obtained (yield=91%) in the form of a yellow oil.

Aufarbeitung

  1. additionadded slowly
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is then washed twice with water
  4. customIt is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f96b34d3a4034574a4881682bfa4bead
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470871B2

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