Diethyl Ether → 2-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanone

HRID 1295955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295955
[C:1]([C:5]1[CH:6]=[C:7]([C:19](=[O:21])[CH3:20])[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.CCOCC>O1CCCC1.C(N(CC)CC)C>[Br:22][CH2:20][C:19]([C:7]1[CH:8]=[C:9]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:10]([O:11][CH3:12])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:21]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 22929663HCID 22929663, Verbindung

Produkt 1

HCID 229297822-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanoneAusbeute 34,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

After dissolving the 1-[3-(tert-butyl)-4-methoxy-5-morpholinophenyl]-1-ethanone (76 g) in tetrahydrofuran (600 ml), triethylamine (110 ml) and tert-butyl dimethylsilyltrifluoromethanesulfonate (75 ml) was added dropwise while cooling on ice. The reaction mixture was stirred for 30 minutes while cooling on ice and then N-bromosuccinimide (70 g) was gradually added. After stirring the reaction mixture for 30 minutes, 2 l of ether was added and the mixture was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (33.7 g) as light yellow crystals.

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. stirringAfter stirring the reaction mixture for 30 minutes
  5. washthe mixture was washed twice with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-41ac5f6af2d74d22af3ed315df5b9426
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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