Iodine chloride → HCID 57423920, compound

HRID 2064080Notes

Reaction equation

HRID 2064080 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].[I:12]Cl.C([O-])(=O)C.[Na+]>C(O)(=O)C>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:8]([I:12])=[C:6]([CH:5]=1)[NH2:7]

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 27741103-(Difluoromethoxy)aniline

Product 1

HCID 57423920HCID 57423920, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[(difluoromethyl)oxy]aniline (3.16 g), iodine monochloride (3.9 g) and sodium acetate (6.5 g) in acetic acid (30 ml) was stirred for 1 hour, then partitioned between saturated sodium bicarbonate solution and ether. The ether layer was separated, washed consecutively with sodium thiosulphate solution and brine. The solvent was removed and the residue was loaded onto a silica gel and chromatographed on silica gel eluted with hexane/ethyl acetate 0-20% to give the title compound as a red oil (2.9 g). Mass Spectrum 286 M+H+

Workup

  1. custompartitioned between saturated sodium bicarbonate solution and ether
  2. customThe ether layer was separated
  3. washwashed consecutively with sodium thiosulphate solution and brine
  4. customThe solvent was removed
  5. customchromatographed on silica gel
  6. washeluted with hexane/ethyl acetate 0-20%

Sources & evidence

ORD record
ord-6dd9bd3588d94237b761d4931977ed46
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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