Ethanol → (3-Bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine

HRID 221922

Reaktionsgleichung

Reaktionsgleichung von HRID 221922
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11].C(N(CC)CC)C.C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:14][CH:13]([O:16][CH2:17][CH3:18])[O:12][CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 82187Benzenamine, 3-bromo-4-methyl-

Produkt 1

HCID 59488813(3-Bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amineAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Under a nitrogen stream, a mixture of 3-bromo-4-methyl-phenylamine (4.94 g, 26.55 mmol), bromoacetaldehyde diethyl acetal (6.80 g, 34.50 mmol), triethylamine (5.37 mL, 38.53 mmol) and ethanol (10.3 mL) was stirred for 2 hours at 150° C. using a microwave apparatus. The resultant solution was cooled to room temperature, and then water was added thereto. The resultant mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:10)), to thereby obtain the titled compound (6.43 g, 80%).

Aufarbeitung

  1. extractionThe resultant mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:10))

Quellen und Nachweise

ORD-Eintrag
ord-1c17dcd5465d4098b149d97cecfc02db
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207134B2

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