Acetone → 4-Bromo-2-{[(3,5-dichlorophenyl)amino]methyl}phenol

HRID 421015

Reaktionsgleichung

Reaktionsgleichung von HRID 421015
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[N:5]=[CH:6][C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:8]=1[OH:14].[BH4-].[Na+].CC(C)=O.O>O1CCCC1.C(O)C>[Br:13][C:11]1[CH:10]=[CH:9][C:8]([OH:14])=[C:7]([CH2:6][NH:5][C:4]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:2]([Cl:1])[CH:3]=2)[CH:12]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 7101644-Bromo-2-{[(3,5-dichlorophenyl)imino]methyl}phenolHCID 4311764Sodium borohydride

Produkt 1

HCID 6772974-Bromo-2-{[(3,5-dichlorophenyl)amino]methyl}phenolAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3,5-Dichloro-N-(5-bromo-2-hydroxybenzylidene)aniline (1.04 g, 3 mmol) was dissolved in tetrahydrofuran (12 mL) and ethanol (6 mL). Sodium borohydride (113 mg, 3 mmol) was added under ice cooling and argon atmosphere, and the mixture was stirred at room temperature for 12 hours. Acetone (10 mL) was added to the reaction mixture, and the residue obtained by concentration under reduced pressure was added water and extracted with dichloromethane. After the dichloromethane layer was washed with water and brine one after another, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give a light yellow viscous material. This was crystallized by n-hexane to give the title compound (971 mg, 93.3%) as a white crystal.

Aufarbeitung

  1. customthe residue obtained by concentration under reduced pressure
  2. extractionextracted with dichloromethane
  3. washAfter the dichloromethane layer was washed with water and brine one after another,
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)
  7. customto give a light yellow viscous material
  8. customThis was crystallized by n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f04ae2982aff4298935d24c12f2c64b8
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097759B2

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