Acetic Acid → 4-Fluoro-2-nitrophenol

HRID 1018791Notes

Reaction equation

HRID 1018791 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(O)(=O)C.[N+:13]([O-])([OH:15])=[O:14]>N([O-])=O.[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 97324-Fluorophenol

Product 1

HCID 1362364-Fluoro-2-nitrophenolYield 85.1%

Reagents, catalysts & solvents 2

HCID 23668193Sodium NitriteCatalystHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

In a 500-ml flask, place 44.8 g (0.4 m) of 4-fluorophenol (1a; X=F) and 132 ml of acetic acid and stir to a solution. Add 0.6 g of sodium nitrite and cool the solution to 15° C. Add 36.0 g (0.4 m) of 70% nitric acid in drop wise keeping the temperature at 22-27° C. over 10-15 min. Stir the resulting yellow slurry at room temperature for 3 hrs. Warm the mixture to 65° C. to make a clear solution and add 132 ml of warm (65° C.) water slowly. Stir the resulting slurry and cool to 15° C. Collect solid, wash with water thoroughly, and dry in air to give 53.4 g (85%) of 4-fluoro-2-nitrophenol (2a; X=F) as yellow granular solids.

Workup

  1. customat 22-27° C.
  2. customover 10-15 min
  3. temperatureWarm the mixture to 65° C.
  4. additionadd 132 ml
  5. stirringStir the resulting slurry
  6. temperaturecool to 15° C
  7. customCollect solid
  8. washwash with water thoroughly
  9. customdry in air

Sources & evidence

ORD record
ord-bf3fb5f94d97446da11b913fdd40d6eb
Source dataset
uspto-grants-2002_11
Patent number
US06482985B1

Reaction notes

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