Nitronium tetrafluoroborate → Methyl 3-(4-nitrophenyl)-1-adamantaneacetate

HRID 21683

Reaction equation

HRID 21683 reaction equation
[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.[O:27]=[N+:28]=[O:29]>C(#N)C>[N+:28]([C:4]1[CH:3]=[CH:2][C:1]([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)=[CH:6][CH:5]=1)([O-:29])=[O:27]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 53665692Methyl 3-phenyl-1-adamantaneacetate

Product 1

HCID 2843871Methyl 3-(4-nitrophenyl)-1-adamantaneacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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) yielded 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.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction was stirred for 45 minutes
  3. additionafter the addition
  4. filtrationThe resulting solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f83bcdbd75e34ea5961abfa57d12f2ab
Source dataset
uspto-grants-1995_06
Patent number
US05424414

Linked notes

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