Iodine → 4-Fluoro-2-iodoaniline

HRID 1283709Notes

Reaction equation

HRID 1283709 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[I:9]I.C(=O)([O-])[O-].[Ca+2].CCOCC>O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 3283Diethyl EtherHCID 97314-FluoroanilineHCID 10112Calcium Carbonate

Product 1

HCID 27782834-Fluoro-2-iodoaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 22 g. of 4-fluoroaniline, 50 g. of iodine, 25 g. of calcium carbonate, 75 ml. of ether and 75 ml. of water is heated at reflux for 48 hours. The ether is removed by distillation and the excess iodine is destroyed by addition of sodium thiosulfate. Steam distillation and recrystallization from petroleum ether gives 4-fluoro-2-iodoaniline.

Workup

  1. additionA mixture of 22 g
  2. temperatureat reflux for 48 hours
  3. customThe ether is removed by distillation
  4. customthe excess iodine is destroyed by addition of sodium thiosulfate
  5. distillationSteam distillation and recrystallization from petroleum ether

Sources & evidence

ORD record
ord-5ff7a42cd670456fba803236cbdc8239
Source dataset
uspto-grants-1976_08
Patent number
USRE028939

Reaction notes

Loading…