Iodine chloride → 2-Fluoro-6-iodo-4-methylaniline

HRID 447751Notes

Reaction equation

HRID 447751 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].O.O.O.C([O-])(=O)C.[Na+].[I:18]Cl.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(OCC)C>[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([I:18])[C:3]=1[NH2:4]

Participants

7

Reactant 4

HCID 24640Iodine chlorideHCID 679842-Fluoro-4-methylanilineHCID 18470521Sodium bicarbonate sodium sulfiteHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 109779002-Fluoro-6-iodo-4-methylaniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-fluoro-4-methylaniline (1.0 g, 8 mmol) (bought from Avocado, Lancaster or Aldrich) in glacial acetic acid (10 ml) was treated with sodium acetate trihydrate (2.2 g, 16 mmol) then iodine monochloride (1.3 g). After 30 min at room temperature aqueous sodium bicarbonate/sodium sulfite and diethyl ether were added, and the organic phase was dried (MgSO4), evaporated and chromatographed on silica eluting with 0 to 30% ethyl acetate in hexane to give the title compound, 370 mg.

Workup

  1. dry with materialthe organic phase was dried (MgSO4)
  2. customevaporated
  3. customchromatographed on silica eluting with 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1321d7bb5ab84781ba885aa67bff8733
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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