Methanol → 2-((4-Bromobenzyl)amino)ethanol

HRID 1792417

Reaktionsgleichung

Reaktionsgleichung von HRID 1792417
CN(CCO)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.[Br:14]Br.C([N:18]([CH2:21]C)CC)C.[C:23]([O:26]CC)(=O)[CH3:24]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C>[Br:14][C:3]1[CH:4]=[CH:5][C:6]([CH2:21][NH:18][CH2:24][CH2:23][OH:26])=[CH:7][CH:8]=1

Komponenten

8

Edukt 5

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 24408Bromine2×HCID 623402-(N-Methylanilino)ethanol

Produkt 1

HCID 4079852-((4-Bromobenzyl)amino)ethanolAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5946Tetraethylammonium ChlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(N-methylanilino)ethanol (0.76 g, 5 mmol) in methylene chloride (5 mL) were added tetraethylammonium chloride (83.0 mg, 0.5 mmol) and 0.1 mL of methanol. While stirring, a solution of bromine (0.8 g, 5 mmol) in methylene chloride (5 mL) was added slowly in a period of 5 minutes. When the color of the bromine persisted, triethylamine (0.75 mL) was added dropwise. The reaction mixture was diluted by ethyl acetate, washed with saturated sodium bicarbonate and brine, dried, and concentrated under reduced pressure to give 1.31 g of crude product which contained some 2,6-dibromo derivative. Flash chromatography of the crude mixture (35% ethyl acetate/hexane) gave 0.87 g (75%) of the desired product.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto give 1.31 g of crude product which

Quellen und Nachweise

ORD-Eintrag
ord-b331bea50b8341399b359a762691f74c
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074819B2

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