Reaktion #69606

Reaktionsgleichung

water

9-bromophenanthrene

tBuLi

9

2-Methoxy-N-[(1E)-phenylmethylene]aniline

→

title product

2-Methoxy-N-[9-phenanthryl(phenyl)methyl]aniline

Lösungsmittel

THF

pentane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis mixture was additionally stirred for 1 hr at this temperature
2. 2
   Temperaturslowly warmed to room temperature
3. 3
   workup.STIRRINGThe resulting mixture was stirred for 30 min at ambient temperature
4. 4
   Temperaturcooled to −80° C
5. 5
   Sonstigethis mixture was evaporated to dryness

Vorschrift

To a solution of 5.14 g (20.0 mmol) of 9-bromophenanthrene in 80 mL of THF, 26.7 mL (40.1 mmol) of 1.5 M tBuLi in pentane was added with vigorous stirring at −80° C. This mixture was additionally stirred for 1 hr at this temperature and then slowly warmed to room temperature. The resulting mixture was stirred for 30 min at ambient temperature and then cooled to −80° C. A solution of 4.22 g (20.0 mol) of 9 in 50 mL of THF was added. To the resulting mixture, 5 mL of water was added, and then this mixture was evaporated to dryness. The title product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.). Yield 7.32 g (94%).

Quelle