Borane;tetrahydrofuran → 3-(Aminomethyl)-4-iodophenol

HRID 2236472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236472
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[C:7]#[N:8].B.C1COCC1>C1COCC1>[NH2:8][CH2:7][C:6]1[CH:9]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[I:10]

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 686960525-Hydroxy-2-iodobenzonitrile

Produkt 1

HCID 593000293-(Aminomethyl)-4-iodophenolAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-Hydroxy-2-iodo-benzonitrile (245 mg, 1 mmol) in THF (3 mL) is added BH3.THF (6 mL, 1 M solution in THF) under N2. The mixture is then allowed to stir at room temperature for 24 hours. The reaction is then quenched with 6N HCl. THF is then removed and the aqueous layer is then neutralized with ammonium hydroxide to pH 9. The mixture is then extracted with CHCl3/MeOH (9:1). The organic layer dried and evaporated and the residue is chromatographed to provide the desired product (80 mg, 32%).

Aufarbeitung

  1. customThe reaction is then quenched with 6N HCl
  2. customTHF is then removed
  3. extractionThe mixture is then extracted with CHCl3/MeOH (9:1)
  4. customThe organic layer dried
  5. customevaporated
  6. customthe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-1e0c066abd264201af02fb95b0cb6613
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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