4-Fluoro-3-nitrobenzyl alcohol → (3-Amino-4-fluorophenyl)methanol

HRID 60624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60624
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-])=O>CCO.[Pd]>[NH2:10][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:2]=1[F:1]

Komponenten

4

Edukt 1

HCID 41675874-Fluoro-3-nitrobenzyl alcohol

Produkt 1

HCID 13563644(3-Amino-4-fluorophenyl)methanolAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

4-Fluoro-3-nitrobenzyl alcohol (3.17 g, 18.5 mmol) was suspended in EtOH, and a slurry of palladium on carbon (10 wt %, 317 mg) in EtOH was added. The flask was sealed with a septum, evacuated, and a H2 filled balloon was introduced via syringe and the reaction was stirred at RT overnight. The reaction mixture was then filtered through a pad of Celite, washed with EtOH and the filtrates concentrated in vacuo to afford a oil which upon scratching crystallised to give the title compound (2.56 g, 98%). 1H NMR (300 MHz, CDCl3): 4.57 (2H, s), 6.63-6.71 (1H, m), 6.77-6.84 (1H, m), 6.90-7.00 (1H, dd, J=8.2, 11.0 Hz). No OH or NH signals observed.

Aufarbeitung

  1. customThe flask was sealed with a septum
  2. customevacuated
  3. additiona H2 filled balloon was introduced via syringe
  4. filtrationThe reaction mixture was then filtered through a pad of Celite
  5. washwashed with EtOH
  6. concentrationthe filtrates concentrated in vacuo
  7. customto afford a oil which
  8. customupon scratching crystallised

Quellen und Nachweise

ORD-Eintrag
ord-c31eabff7bd544f5919c19332b3a6c04
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440974B2

Notizen zur Reaktion

Wird geladen…