Triethylamine → N-(2-hydroxy-5-bromophenyl)-3,3-dimethylbutyramide

HRID 48166

Reaktionsgleichung

Reaktionsgleichung von HRID 48166
[C:1]([CH2:5][C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[OH:17].C(N(CC)CC)C>C(OCC)C>[OH:17][C:11]1[CH:12]=[CH:13][C:14]([Br:16])=[CH:15][C:10]=1[NH:9][C:6](=[O:7])[CH2:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 3518402-Amino-4-Bromophenol

Produkt 1

HCID 22742126N-(2-hydroxy-5-bromophenyl)-3,3-dimethylbutyramideAusbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of tert-butylacetyl chloride (2.7 g, 0.020 mol) in diethyl ether (20 ml) was added dropwise to a solution of 2-amino-4bromophenol (3.8 g, 0.020 mol) and triethylamine (2.1 g, 0.020 mol) in diethyl ether (160 ml) and the mixture was stirred at room temperature for 3 hours. The mixture was filtered and the filtrate was evaporated in vacuo. Purification by flash column chromatography on silica gel, eluting initially with ethyl acetate:dichloromethane 1.5:98.5 and then with ethyl acetate:dichloromethane 2.5:97.5, gave N-(2-hydroxy-5-bromophenyl)-3,3-dimethylbutyramide (1.8 g).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customPurification by flash column chromatography on silica gel
  4. washeluting initially with ethyl acetate:dichloromethane 1.5:98.5

Quellen und Nachweise

ORD-Eintrag
ord-a4dae2ba05c94e56acd37a42b6eece85
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703347B2

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