Potassium Iodide → 2-Chloro-4-iodo-1-trifluoromethylbenzene

HRID 1096193

Reaction equation

HRID 1096193 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])N.C1(C)C=CC(S(O)(=O)=O)=CC=1.[I-:24].[K+].N([O-])=O.[Na+].C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC#N.O>[Cl:1][C:2]1[CH:3]=[C:4]([I:24])[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 6101p-Toluenesulfonic acidHCID 24477Sodium ThiosulfateHCID 679623-Chloro-4-(trifluoromethyl)anilineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 667832122-Chloro-4-iodo-1-trifluoromethylbenzeneYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-4-(trifluoromethyl)aniline (450 mg, 2.30 mmol) and toluene 4-sulfonic acid (1.19 g, 6.92 mmol) in CH3CN (10 mL) was added a solution of potassium iodide (955 mg, 5.76 mmol) and sodium nitrite (318 mg, 4.61 mmol) in water (1.8 mL) over 15 min at 10° C., then after 20 min the reaction mixture was poured onto water, neutralized with sat. aq. NaHCO3 solution, treated with 2 M aq. sodium thiosulfate solution (6 mL), and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (517 mg) as a light brown oil, which was directly used in the next step.

Workup

  1. additionafter 20 min the reaction mixture was poured onto water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7ef7172636944e12b9986b5fd24a4f94
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Linked notes

Loading…