4-tert-Butyltoluene → 4-Tert-butyl-1-methyl-2-nitrobenzene

HRID 1294471Notes

Reaction equation

HRID 1294471 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.[O:17]=[N+:18]=[O:19]>C(#N)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[C:9]([N+:18]([O-:19])=[O:17])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 73904-tert-ButyltolueneHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 109544154-Tert-butyl-1-methyl-2-nitrobenzeneYield 58.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-tert-butyl toluene (5 g, 33.7 mmol) in acetonitrile (150 mL) at 0° C. was added nitronium tetrafluoroborate (5.83 g, 40.5 mmol). After 30 min at room temperature, the reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine and dried (MgSO4). Removal of the volatiles in vacuo left a residue which was purified by flash chromatography using 10% methylene chloride in petroleum ether as eluent. Concentration in vacuo of the product rich fractions provided 3.8 g of 4-tert-butyl-2-nitrotoluene.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of the volatiles in vacuo
  5. waitleft a residue which
  6. customwas purified by flash chromatography
  7. concentrationConcentration in vacuo of the product rich fractions

Sources & evidence

ORD record
ord-5cc38198e1ac4afe8760cc5767239d1b
Source dataset
uspto-grants-2007_07
Patent number
US07241758B2

Reaction notes

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