Hydrofluoric Acid → 2,4-Difluoroaniline

HRID 614506Notes

Reaction equation

HRID 614506 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[N+]=[N-].[FH:11]>C1CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:11])[CH:5]=[CH:4][C:3]=1[NH2:8]

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 116079241-Azido-2-fluorobenzene

Product 1

HCID 97092,4-Difluoroaniline

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of 4.11g. (0.03 mole) of 2-fluorophenylazide in 81 ml. of cyclohexane was treated with 20 ml. of hydrogen fluoride. The reaction mixture was then shaken at room temperature for 24 hours, then cooled, vented, and rinsed from the bomb with two successive applications of 100 ml. of dichloromethane and then 100 ml. of water. The reaction mixture was then blown down under nitrogen, quenched in 75g. of ice, and rendered basic with KOH pellets. The reaction mixture was extracted with dichloromethane to yield 2.2g. (57%) of a brown-red fluid after drying over MgSO4. The 2,4-difluoroaniline structure of the final product was confirmed by IR, and the product had a b.p. of 90°-92° C. at 40 mm. Hg.

Workup

  1. temperaturecooled
  2. washrinsed from the bomb with two successive applications of 100 ml
  3. customquenched in 75g
  4. extractionThe reaction mixture was extracted with dichloromethane
  5. customto yield 2.2g
  6. dry with material(57%) of a brown-red fluid after drying over MgSO4

Sources & evidence

ORD record
ord-4ef65dd388a940f0ab3d8f8fd72b88ba
Source dataset
uspto-grants-1979_03
Patent number
US04145364

Reaction notes

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