Sulfuric Acid → 4-Fluorobenzenediazonium hydrogensulphate

HRID 36781Notes

Reaction equation

HRID 36781 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[S:9](=[O:13])(=[O:12])([OH:11])[OH:10].[N:14]([O-])=O.[Na+].NC(N)=O>O>[S:9]([O-:13])([OH:12])(=[O:11])=[O:10].[F:1][C:2]1[CH:8]=[CH:7][C:5]([N+:6]#[N:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 97314-FluoroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 139552264-Fluorobenzenediazonium hydrogensulphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Fluoroaniline (11.2 g; 0.1 mol) was added dropwise into a solution of sulphuric acid (25 g) in water (60 ml) over 10 min. A smooth paste was formed. The mixture was cooled to <5° and a solution of sodium nitrite (7.8 g; 0.11 mol) in water (25 ml) was added dropwise over 0.5 hours while maintaining the temperature at <5° with external cooling. A clear red solution was obtained. The solution was stirred for 0.25 hours to complete the reaction and urea (1.0 g) was added to destroy the excess nitrous acid. The resulting solution was used directly in the next stage.

Workup

  1. customA smooth paste was formed
  2. temperatureThe mixture was cooled to <5°
  3. temperaturewhile maintaining the temperature at <5° with external cooling
  4. customA clear red solution was obtained
  5. additionwas added
  6. customto destroy the excess nitrous acid

Sources & evidence

ORD record
ord-80ec530aebed4d97b9df6f3bc2ca43d1
Source dataset
uspto-grants-1995_05
Patent number
US05416235

Reaction notes

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