Sodium borohydride → 2-(2-Fluoro-4-nitrophenyl)ethan-1-ol

HRID 1842954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842954
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12](OC)=[O:13].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 18369150Methyl 2-Fluoro-4-nitrophenylacetate

Produkt 1

HCID 866721582-(2-Fluoro-4-nitrophenyl)ethan-1-olAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred solution of methyl 2-(2-fluoro-4-nitrophenyl)acetate (3.0 g, 14.0 mmol, 1.0 eq) in methanol (30 mL) was added NaBH4 (2.08 g, 36.3 mmol, 4.0 eg) at 0° C. and stirred at 70° C. for 16 h, then the methanol was evaporated and the residue was diluted with water (30 mL), the pH adjusted to being neutral with 2N HCl and the mixture extracted with EtOAc (50 mL×3). The organic layer was separated, washed with brine, dried over Na2SO4 and the solvent evaporated to yield 2-(2-fluoro-4-nitrophenyl)ethanol (2.0 g, 77%) as a viscous oil (TLC system: EtOAc/PE (3:7), Rf: 0.3).

Aufarbeitung

  1. customthe methanol was evaporated
  2. additionthe residue was diluted with water (30 mL)
  3. extractionthe mixture extracted with EtOAc (50 mL×3)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2fe3bc86216640c5a2587b8ddce146db
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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