Methane → 4-Amino-2,3-difluorophenol

HRID 1955372Notes

Reaction equation

HRID 1955372 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[N:10]=NC1C=CC=CC=1.[H][H].C>CO>[OH:9][C:6]1[CH:5]=[CH:4][C:3]([NH2:10])=[C:2]([F:1])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 297MethaneHCID 1355741042,3-Difluoro-4-(2-phenyldiazenyl)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 27787664-Amino-2,3-difluorophenolYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, 3.5 g (0.015 mol) of (2,3-difluoro-4-hydroxyphenyl)-phenyldiazene are dissolved in 30 ml of methanol in a 100 ml three-neck flask fitted with internal thermometer, stirrer and gas inlet tube. The flask is flushed with argon, and 1.5 g of Raney nickel and 25 μl of bis(2-hydroxyethyl) sulphide are then added. 692 ml of hydrogen (0.03 mol) are then applied at room temperature with a pressure of about 1 bar. The reaction mixture is admixed with activated charcoal, stirred for a further 15 minutes and filtered over a bed of silica gel. The solvent is distilled off and the residue is washed with n-hexane, affording 2.0 g (91.9% of theory) of 4-hydroxy-2,3-difluoroaniline.

Workup

  1. customfitted with internal thermometer, stirrer and gas inlet tube
  2. customThe flask is flushed with argon, and 1.5 g of Raney nickel and 25 μl of bis(2-hydroxyethyl) sulphide
  3. additionare then added
  4. customare then applied at room temperature with a pressure of about 1 bar
  5. filtrationfiltered over a bed of silica gel
  6. distillationThe solvent is distilled off
  7. washthe residue is washed with n-hexane

Sources & evidence

ORD record
ord-00c676e393a14cc9abc82e8aa98db9ac
Source dataset
uspto-grants-2000_09
Patent number
US06124504

Reaction notes

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