Reaktion #73759

Reaktionsgleichung

H2SO4

40

(3-Bromophenyl)(4-methylphenyl)methanone

Si(OEt)4

2,6-diisopropylaniline

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title product

Ausbeute 84.0%

N-[(3-Bromophenyl)(4-methylphenyl)methylene]-2,6-diisopropylaniline

Ausbeute 84.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONthe formed ethanol was slowly distilled off
2. 2
   workup.ADDITIONFurther on, 300 mL of cold water was added
3. 3
   Extraktionthe product was extracted with 2×100 mL of diethyl ether
4. 4
   ExtraktionThe combined extract
5. 5
   Trocknenwas dried over K2CO3
6. 6
   Sonstigeevaporated 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, 100:1, vol.)

Vorschrift

In 50 mL Claisens flask in an argon atmosphere, a mixture of 9.63 g (35.0 mmol) of 40, 8.75 g (42.0 mmol) of Si(OEt)4, and 6.83 g (38.5 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.23 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 55 hr, and the formed ethanol was slowly distilled off. Further on, 300 mL of cold water was added, and the product was extracted with 2×100 mL of diethyl ether. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.) to give 12.7 g (84%) of the title product.

Quelle