Sodium hydride → 3-(o-Bromobenzyloxy)4-methoxybenzonitrile

HRID 1871489

Reaktionsgleichung

Reaktionsgleichung von HRID 1871489
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#[N:17]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#[N:17]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 728502-Bromobenzyl alcoholHCID 27745483-Fluoro-4-methoxybenzonitrile

Produkt 1

HCID 227070173-(o-Bromobenzyloxy)4-methoxybenzonitrileAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-bromobenzyl alcohol (16.50 g, 88.2 mmol) in DMF (100 ml) was added sodium hydride (60% dispersion in mineral oil, 2.94 g, 73.5 mmol) and this was followed by 3-fluoro-4-methoxybenzonitrile (8.88 g, 58.8 mmol) and the resulting mixture was heated to 90° C. for 2 h under N2. After cooling, the mixture was partitioned between ether and H2O, the organic layer washed sequentially with 0.5N HCl and saturated brine and then dried over MgSO4. Trituration with ether/pentane (1/, v/v) afforded the subtitle compound as an off-white solid (13.35 g, 71%). Rf 0.27 (hexane/EtOAc 5/1, v/v). MS m/z 318, 320 (MH+).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ether and H2O
  3. washthe organic layer washed sequentially with 0.5N HCl and saturated brine
  4. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-725f9954f649420c8fe12b745486b187
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103738

Verknüpfte Notizen

Wird geladen…