1-Methyl-3-p-tolyltriazene → 2,6-Difluoro-4-nitroanisole

HRID 1666823Notes

Reaction equation

HRID 1666823 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[OH:12].[CH3:13]N=NNC1C=CC(C)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 304921-Methyl-3-p-tolyltriazeneHCID 6002102,6-Difluoro-4-nitrophenol

Product 1

HCID 6050602,6-Difluoro-4-nitroanisole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Dissolve 2,6-difluoro-4-nitrophenol (J. Heterocyclic. Chem. 1976, 13, 1253; 10 g, 57.11 mmol) in 300 mL of benzene. Add dropwise a solution of 1-methyl-3-p-tolyltriazene (9.37 g, 62.82 mmol, 1.1 eq.) in benzene (150 mL). After TLC indicates absence of starting material, transfer the reaction mixture to a separator funnel and wash with 1 N HCl, then saturated NaHCO3, and then water. Dry the organic layer over MgSO4, filter, and remove the solvent to give a residue. Crystallize the residue from MeOH/water to give 1,3-difluoro-2-methoxy-5-nitrobenzene as white needles: 1H NMR (300 MHz, CDCl3): 4.25 (t, 3H), 7.80 (d, 2H).

Workup

  1. washwash with 1 N HCl
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customremove the solvent
  5. customto give a residue
  6. customCrystallize the residue from MeOH/water

Sources & evidence

ORD record
ord-54cbae742e8c48b89410d61bd9dd4efc
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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