Methanol → 2-(2-Fluoro-5-nitrophenyl)ethanol

HRID 64344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64344
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:12](O)=[O:13].CO>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 8493592-(2-Fluoro-5-nitrophenyl)acetic acid

Produkt 1

HCID 248284032-(2-Fluoro-5-nitrophenyl)ethanolAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-(2-fluoro-5-nitrophenyl)acetic acid (2.0 g, 10 mmol) in THF (50 mL) was added borane dimethyl sulfide complex solution (4.0 g, 25 mmol). The reaction was warmed to 60° C. stirred for about 12 hr. After cooling down to RT, CH3OH (20 mL) was slowly added to the reaction, concentrated under reduced pressure to remove solvent. The residue was purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1) to afford the product as a colorless oil (1.6 g, 86.1%). 1H NMR (400 MHz, DMSO-d6) δ 8.27 (t, J=3.2, 6.4 Hz, 1 H), 8.19-8.14 (m, 1 H), 8.45 (t, J=9.2 Hz, 1 H), 4.80 (t, J=5.6 Hz, 1 H), 3.66 (dt, J=5.6, 6.4 Hz, 1 H), 2.86 (t, J=6.4 Hz, 2 H). MS (ESI) m/e [M+1]+ 186.

Aufarbeitung

  1. temperatureAfter cooling down to RT
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. customThe residue was purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-6531ebd2a299490dbb8aedcb697991e7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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