Sulfuric Acid → 2-Fluoro-5-nitrophenol

HRID 442262Notes

Reaction equation

HRID 442262 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1N.S(=O)(=O)(O)[OH:13].N([O-])=O.[Na+]>O>[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[OH:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 677852-Fluoro-5-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 234981002-Fluoro-5-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3.2 grams of 2-fluoro-5-nitroaniline, sulfuric acid (3 cc., d 1.84) and 8 ml. of water is stirred into a solution of 1.5 grams of sodium nitrite in water, maintained below 5° C. After 10 minutes, the excess nitrous acid is destroyed by urea, the reaction mixture filtered, and the filtrate added to 40 ml. of boiling 50% sulfuric acid. After complete addition, the mixture is boiled an additional 15 minutes, cooled, and the separated phenol filtered and washed with water. It is then purified by recrystallization from hexane.

Workup

  1. temperaturemaintained below 5° C
  2. customthe excess nitrous acid is destroyed by urea
  3. filtrationthe reaction mixture filtered
  4. additionthe filtrate added to 40 ml
  5. additionAfter complete addition
  6. waitthe mixture is boiled an additional 15 minutes
  7. temperaturecooled
  8. filtrationthe separated phenol filtered
  9. washwashed with water
  10. customIt is then purified by recrystallization from hexane

Sources & evidence

ORD record
ord-fed36315ec014f7389cccb24ba93d240
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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