Pentamethylbenzene → HCID 596025, compound

HRID 2229909Notes

Reaction equation

HRID 2229909 reaction equation
[CH3:1][C:2]1[C:3]([CH3:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1.F[B-](F)(F)F.O=[N+:18]=O>ClCCl>[CH3:8][C:6]1[C:7]([NH2:18])=[C:2]([CH3:1])[C:3]([CH3:11])=[C:4]([CH3:10])[C:5]=1[CH3:9]

Participants

4

Reactant 2

HCID 12784PentamethylbenzeneHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 596025HCID 596025, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pentamethylbenzene (5 g, 33.8 mmol) in dichloromethane (250 mL) at 0° C. was quickly added nitronium tetrafluoroborate (5 g). The mixture was stirred for 4 h before it was quenched with cold water. The organic layer was concentrated and the residue was reduced (Example 14, procedure C) to give pentamethylaniline in 52% yield.

Workup

  1. customat 0° C.
  2. customwas quenched with cold water
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-1020288b1a094aadade8f1e748e8debe
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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