Reaktion #73712

Reaktionsgleichung

water

34

2-Bromo-6-[(E)-[(2,6-diisopropylphenyl)imino](phenyl)methyl]-4-methylphenol

nBuLi

2-bromoanisole

→

yellowish solid

Ausbeute 26.0%

3-[(E)-[(2,6-Diisopropylphenyl)imino](phenyl)methyl]-2′-methoxy-5-methylbiphenyl-2-ol

Ausbeute 26.0%

Lösungsmittel

—

hexanes

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was slowly warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 30 min
3. 3
   TemperaturThis mixture was refluxed for 8 hr
4. 4
   WaschenThe silica gel layer was additionally washed with 30 mL of dichloromethane
5. 5
   WaschenThe combined organic elute
6. 6
   Sonstigewas evaporated to dryness
7. 7
   SonstigeThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 20:1, vol.)

Vorschrift

To a solution of 2.25 g (5.0 mmol) of 34 in 20 mL of THF, 4.0 mL (10.0 mmol) of 2.5 M nBuLi in hexanes was added at −80° C. This mixture was stirred for 1 hr, then cooled to −100° C. and 10.8 mL (10.8 mmol) of 1.0 M ZnCl2 in THF was added. The resulting mixture was slowly warmed to ambient temperature, stirred for 30 min, and then 2.82 g (15.0 mmol) of 2-bromoanisole and 0.14 g (0.25 mmol) of Pd(PtBu3)2 was added. This mixture was refluxed for 8 hr, then 5 mL of water was added. The resulting mixture was passed through a short layer of silica gel 60. The silica gel layer was additionally washed with 30 mL of dichloromethane. The combined organic elute was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 20:1, vol.) to give 0.55 g (26%) of a yellowish solid.

Quelle