Acetic Acid → 1-Bromo-2-fluoro-4-iodobenzene

HRID 1755621Notes

Reaction equation

HRID 1755621 reaction equation
N([O-])=O.[Na+].C(O)(=O)C.[F:9][C:10]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:11]=1N.O.[BrH:19]>S(=O)(=O)(O)O.[Cu]Br>[Br:19][C:11]1[CH:13]=[CH:14][C:15]([I:17])=[CH:16][C:10]=1[F:9]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 1856942-Fluoro-4-iodoanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27250061-Bromo-2-fluoro-4-iodobenzene

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 1118Sulfuric AcidSolvent

Procedure

51.2 g of sodium nitrite was dissolved in 390 ml of sulfuric acid, and 454 ml of acetic acid was added thereto at 10° C. or lower. The solution was kept at 20° to 25° C., and 124 g of 2-fluoro-4-iodoaniline was added thereto over a period of one hour and stirred for 2 hours. The solution was dropwise added to a solution of 130 g of copper(I) bromide as dissolved in 390 ml of 48% hydrobromic acid and stirred overnight. Next, 1000 ml of water was added to this, which was then extracted with chloroform and washed three times with water. Chloroform was removed by distillation, and the residue was distilled under reduced pressure (b.p. 120° to 125° C./13 mmHg) and recrystallized from methanol to obtain 114 g of 1-bromo-2-fluoro-4-iodobenzene.

Workup

  1. customat 10° C.
  2. customwas kept at 20° to 25° C.
  3. stirringstirred overnight
  4. extractionwas then extracted with chloroform
  5. washwashed three times with water
  6. customChloroform was removed by distillation
  7. distillationthe residue was distilled under reduced pressure (b.p. 120° to 125° C./13 mmHg)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-583e844bc18641338695df38b7c222ec
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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