Boron tribromide → 3-(3-Hydroxyphenyl)propanenitrile

HRID 1958848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958848
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 100348983-(3-Methoxyphenyl)propanenitrile

Produkt 1

HCID 17123123-(3-Hydroxyphenyl)propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na7SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.

Aufarbeitung

  1. waitat 0° C. for 4 hours
  2. customuntil all the starting material is consumed
  3. customquenched with ice
  4. extractionextracted with EtOAc (30 ml×3)
  5. washthe combined organic layer was washed carefully with sat NaHCO3, brine
  6. dry with materialdried over Na7SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-1439af800df94d5cb89edae8982ccf59
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410154B2

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