Ethyl Acetate → 2-Methoxy-1,3-dinitro-5-(trifluoromethyl)benzene

HRID 985460Notes

Reaction equation

HRID 985460 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].C[O-].[Na+].C[CH2:22][O:23]C(C)=O>CS(C)=O.CO>[CH3:22][O:23][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 10942334Sodium Methoxide

Product 1

HCID 28040782-Methoxy-1,3-dinitro-5-(trifluoromethyl)benzene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

2-Chloro-1,3-dinitro-5-trifluoromethyl-benzene (5.43 g, 20.1 mmol) was dissolved in 10 mL anhydrous DMSO. Sodium methoxide (5.85 mL of a 25% w/w solution in methanol) was added by syringe. The yellow solution immediately turned pink-orange, with heat evolved. The reaction was left stirring overnight at room temperature, then EtOAc (300 mL) was added and the mixture was washed once with dilute HCl aqueous solution, thrice with water and once with brine. The organic solution was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified through a short plug of silica gel and 4.65 g of 2-methoxy-1,3-dinitro-5-trifluoromethylbenzene was isolated as a yellow solid.

Workup

  1. temperatureThe yellow solution immediately turned pink-orange, with heat
  2. waitThe reaction was left
  3. washthe mixture was washed once with dilute HCl aqueous solution, thrice with water and once with brine
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified through a short plug of silica gel

Sources & evidence

ORD record
ord-4b977f2fce8b451c858530c8004b36ba
Source dataset
uspto-grants-2005_03
Patent number
US06872726B2

Reaction notes

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