Ethyl Acetate → 2,4-Dimethoxy-5-fluoronitrobenzene

HRID 990849Notes

Reaction equation

HRID 990849 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[O-]S(C(F)(F)[F:19])(=O)=O.ClC1C=[N+](F)C=C(Cl)C=1.C(OCC)(=O)C>ClCC(Cl)(Cl)Cl>[F:19][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 786332,4-Dimethoxy-1-nitrobenzeneHCID 27245783,5-Dichloro-1-fluoropyridinium triflate2×

Product 1

HCID 27584142,4-Dimethoxy-5-fluoronitrobenzene

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2,4-dimethoxy-nitrobenzene (1.0 g) in tetrachloroethane (10 mL) is added 3,5-dichloro-1-fluoro-pyridinium triflate (85%, 5.07 g) and the mixture is heated to 120° C. for 5 hours. Additional 3,5-dichloro-1-fluoro-pyridinium triflate (85%, 0.25 g) is added and heating is continued for 1 hour. The solution is then cooled to room temperature and passed over a column of silica gel (hexanes followed by 30% ethyl acetate in hexanes is used as the eluant). Product containing fractions are combined, evaporated under reduced pressure, and the residue is crystallized from hexanes to provide the desired product as a tan solid.

Workup

  1. temperatureheating
  2. temperatureThe solution is then cooled to room temperature
  3. additionProduct containing fractions
  4. customevaporated under reduced pressure
  5. customthe residue is crystallized from hexanes

Sources & evidence

ORD record
ord-16f5616d5b2f42dc817be533eb899293
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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