Hydrochloric Acid → 3,4-difluoro-5-methoxybenzenamine

HRID 1625115Notes

Reaction equation

HRID 1625115 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[C:6](F)[C:7]=1[F:8].Cl.C(Cl)Cl.[C:15]([O-])([O-])=[O:16].[Na+].[Na+]>C[O-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[C:6]([O:16][CH3:15])[C:7]=1[F:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27249913,4,5-Trifluoroaniline

Product 1

HCID 581887893,4-difluoro-5-methoxybenzenamine

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 3,4,5-trifluorobenzenamine (40 g; 272 mmol) in NaOMe (30% in MeOH) (250 ml) was heated at reflux for 16 h. The reaction mixture was then poured onto ice with 37% aqueous HCl (150 ml)( ). CH2Cl2 was added and the pH of the reaction mixture was adjusted to pH=7-8 using an aqueous solution of Na2CO3. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by column chromatography over silica gel (eluent: 50:50 heptane/CH2Cl2 to pure CH2Cl2). The pure fractions were collected and the solvent evaporated in vacuo.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by column chromatography over silica gel (eluent: 50:50 heptane/CH2Cl2 to pure CH2Cl2)
  8. customThe pure fractions were collected
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f4830a596d7346f9a39546fe972627ef
Source dataset
uspto-grants-2014_07
Patent number
US08779158B2

Reaction notes

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