Hydrogen Peroxide → 2-amino-3-fluorophenol

HRID 1655094Notes

Reaction equation

HRID 1655094 reaction equation
FC1C=CC=C(F)C=1C#[N:5].[OH-].[Na+].OO.C([O:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:24]=1C(N)=O)C1C=CC=CC=1.ClCl>C(O)C1C=CC=CC=1.O>[NH2:5][C:24]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:23]=1[OH:22]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 24526ChlorineHCID 746952,6-DifluorobenzonitrileHCID 152191982-Fluoro-6-(phenylmethoxy)benzamide

Product 1

HCID 27827782-amino-3-fluorophenolYield 51%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 962WaterSolvent

Procedure

69.9 g (0.5 mol) of 2,6-difluorobenzonitrile and 237 g (1.2 mol) of 6-normal sodium hydroxide solution are initially introduced in 200 ml of benzyl alcohol. 221 g (1.95 mol) of 30% hydrogen peroxide solution are added dropwise to this mixture within the space of 30 min, the temperature rising from 20° C., at the beginning of the metering-in, to 50° C., and then being maintained at this value. After 5 h (complete transformation to 2-benzyloxy-6-fluorobenzamide can be demonstrated by GC), the mixture is cooled and supplemented with 200 g of water and 60 g (1.5 mol) of sodium hydroxide. Chlorine is passed in (8-10 l/h) at 30° C. for 2 h, with the reaction being monitored by gas chromatography and terminated once the amide has disappeared. The phases are separated, 180 g of methanol are added to the organic phase, and further processing is carried out as indicated in Example 8. 32.4 g (0.255 mol, 51%) of 2-amino-3-fluorophenol are obtained as a brown-black powder.

Workup

  1. customrising from 20° C., at the beginning
  2. customto 50° C.
  3. temperaturebeing maintained at this value
  4. temperaturethe mixture is cooled
  5. customterminated once the amide
  6. customThe phases are separated
  7. addition180 g of methanol are added to the organic phase, and further processing

Sources & evidence

ORD record
ord-b7a270b5dbcd47098d203ac4184d0d78
Source dataset
uspto-grants-1995_04
Patent number
US05410082

Reaction notes

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