Sulfuric Acid → 4-Amino-3-fluorophenol

HRID 1200166Notes

Reaction equation

HRID 1200166 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[Al].S(=O)(=O)(O)[OH:13].C(=O)([O-])O.[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([OH:13])[CH:5]=[CH:4][C:3]=1[NH2:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium BicarbonateHCID 5359268Aluminum

Product 1

HCID 27359194-Amino-3-fluorophenolYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.03 Grams of o-fluoronitrobenzene, 0.70 g of aluminum powder, 43 ml of water and 4.4 g of conc. sulfuric acid were added to a reactor and stirred at an inner temperature of from 90° to 95° C. for 40 minutes. After cooling the reaction solution, a 5% aqueous sodium hydrogencarbonate solution was added to make the reaction solution weakly alkaline. The reaction solution was then extracted with three 100-ml portions of diethyl ether. The ether layers were combined, dried and concentrated to obtain a crude product. This crude product was subjected to chromatography on silica gel to obtain 1.58 g of 3-fluoro-4-aminophenol.

Workup

  1. temperatureAfter cooling the reaction solution
  2. extractionThe reaction solution was then extracted with three 100-ml portions of diethyl ether
  3. customdried
  4. concentrationconcentrated
  5. customto obtain a crude product

Sources & evidence

ORD record
ord-f4f64ae98df14153a677414a0f935a72
Source dataset
uspto-grants-1990_02
Patent number
US04904696

Reaction notes

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