Nitric Acid → 4-Chloro-2-fluoro-5-nitroaniline

HRID 651905Notes

Reaction equation

HRID 651905 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:8]([N+:10]([O-:12])=[O:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 137530614-Chloro-2-fluoro-5-nitroanilineYield 66.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Chloro-2-fluoroaniline (23 g) was dissolved in conc. sulfuric acid (120 ml), and the resultant mixture was cooled to -20° C., followed by dropwise addition of fuming nitric acid (15 g). The reaction mixture was stirred at -20° to -15° C. for 1.5 hours, poured into ice-water and then extracted with ether. The ether extract was washed with water and a saturated sodium bicarbonate solution, dried and concentrated. The residue was crystallized from a mixture of toluene and hexane (2:1) to obtain 20 g of 4-chloro-2-fluoro-5-nitroaniline. m.p., 83°-84.5° C.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with water
  4. dry with materiala saturated sodium bicarbonate solution, dried
  5. concentrationconcentrated
  6. customThe residue was crystallized from a mixture of toluene and hexane (2:1)

Sources & evidence

ORD record
ord-65207d958f6b4a8f829a797462027232
Source dataset
uspto-grants-1987_06
Patent number
US04670043

Reaction notes

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