Réaction #73759

Équation de réaction

H2SO4

40

(3-Bromophenyl)(4-methylphenyl)methanone

Si(OEt)4

2,6-diisopropylaniline

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title product

Rendement 84.0%

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

Rendement 84.0%

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONthe formed ethanol was slowly distilled off
2. 2
   workup.ADDITIONFurther on, 300 mL of cold water was added
3. 3
   Extractionthe product was extracted with 2×100 mL of diethyl ether
4. 4
   ExtractionThe combined extract
5. 5
   Séchagewas dried over K2CO3
6. 6
   Autreevaporated to dryness
7. 7
   AutreThe product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.)

Mode opératoire

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.

Source