Reaktion #1256883

Reaktionsgleichung

triphenyl phosphine

DEAD

1-(2,6-dichloro-3-fluoro-phenyl)-ethanol

3-hydroxy-nitropyridine

→

3-(2,6-dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine

Ausbeute 100.0%

Lösungsmittel

toluene

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigehad been consumed
2. 2
   SonstigeThe solvent was removed
3. 3
   Trocknenthe crude material was dry
4. 4
   Wascheneluted with ethyl acetate-hexanes (20:80)

Vorschrift

To a stirred solution of triphenyl phosphine (8.2 g, 0.03 mol) and DEAD (13.65 mL of a 40% solution in toluene) in THF (200 mL) at 0° C. was added a solution of 1-(2,6-dichloro-3-fluoro-phenyl)-ethanol (4.55 g, 0.021 mol) and 3-hydroxy-nitropyridine (3.35 g, 0.023 mol) in THF (200 mL). The resulting bright orange solution was stirred under a nitrogen atmosphere at ambient temperature for 4 hours at which point all starting materials had been consumed. The solvent was removed, and the crude material was dry loaded onto silica gel, and eluted with ethyl acetate-hexanes (20:80) to yield 3-(2,6-dichloro-3-fluoro-benzyloxy)-2-nitro-pyridine (6.21 g, 0.021 mol, 98%) as a pink solid. 1H NMR (CDCl3, 300 MHz) 1.8-1.85 (d, 3H), 6.0-6.15 (q, 1H), 7.0-7.1 (t, 1H), 7.2-7.21 (d, 1H), 7.25-7.5 (m, 2H), 8.0-8.05 (d, 1H).

Quelle