반응 #80262

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Methyl 3-phenyl-1-adamantaneacetate

Nitronium tetrafluoroborate

→

methyl 3-(4-nitrophenyl)-1-adamantaneacetate

용매

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   workup.STIRRINGThe reaction was stirred for 45 minutes
3. 3
   workup.ADDITIONafter the addition
4. 4
   여과The resulting solid was collected by filtration
5. 5
   기타dried in vacuo

실험 절차

Methyl 3-phenyl-1-adamantaneacetate, example 1, (78.8 g) was dissolved in acetonitrile (800 mL) and cooled in an ice bath while stirring under a nitrogen atmosphere. Nitronium tetrafluoroborate (40.8 g) in acetonitrile (800 mL) was added dropwise over 45 minutes. The reaction was stirred for 45 minutes after the addition, then poured into ice (985 g). The resulting solid was collected by filtration and dried in vacuo to give methyl 3-(4-nitrophenyl)-1-adamantaneacetate (55.9 g). Mass spectrum: (M+NH4)+ @347. Extraction of the aqueous phase with t-butyl methyl ether (2×800 mL) yeilded additional material including the lesser products, methyl 3-(2-nitrophenyl)-1-adamantaneacetate; Mass spectrum: (M+NH4)+ @347 and methyl 3-(2,4-dinitrophenyl)-1-adamantaneacetate; Mass spectrum: (M+NH4)+ @392.

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