Boron tribromide → 5-Amino-2-cyclopropylphenol

HRID 471955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471955
B(Br)(Br)Br.[CH:5]1([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[O:15]C)[CH2:7][CH2:6]1>ClCCl>[NH2:12][C:11]1[CH:13]=[CH:14][C:8]([CH:5]2[CH2:7][CH2:6]2)=[C:9]([OH:15])[CH:10]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 593949554-cyclopropyl-3-Methoxyaniline

Produkt 1

HCID 552846985-Amino-2-cyclopropylphenolAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of BBr3 in dichloromethane (4.47 mL of 1 M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN 0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+.

Aufarbeitung

  1. washThe reaction mixture was washed with aqueous NaHCO3, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by HPLC (10-99% CH3CN 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-6f6f9cd66a164c26bc5edcbbc8c04c4b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633189B2

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