Water → 3-(3-Bromo-4-fluorophenyl)propanenitrile

HRID 705799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705799
[Br:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 61702072(E)-3-(3-Bromo-4-fluorophenyl)acrylonitrile

Produkt 1

HCID 534343013-(3-Bromo-4-fluorophenyl)propanenitrileAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of (E)-3-(3-bromo-4-fluorophenyl)acrylonitrile (35.0 g, 108 mmol) in ethanol (20 mL) at 0° C. was added sodium tetrahydroborate (16.40 g, 434 mmol). The reaction mixture was allowed to warm to 70° C. and stirred for 4 h. Water was added to quench the reaction, and the organic layer was separated. The water layer was extracted with DCM twice, and the combined organic phase was dried and concentrated. The residue was purified by chromatography to afford the title compound as an oil (20 g, 64.7% yield). LCMS: rt=1.45 min, [M+H+]=228

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. customthe organic layer was separated
  4. extractionThe water layer was extracted with DCM twice
  5. customthe combined organic phase was dried
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7bae86022e174a06989fd226a8c83e4e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

Notizen zur Reaktion

Wird geladen…