Potassium Iodide → 4-Fluoro-2-iodo-1-nitrobenzene

HRID 419351Notes

Reaction equation

HRID 419351 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)N.N([O-])=O.[Na+].[I-:16].[K+]>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([I:16])[CH:8]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 753995-Fluoro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 193619484-Fluoro-2-iodo-1-nitrobenzeneYield 83%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 5-fluoro-2-nitroaniline (70.0 g, 448 mmol) in HCl (350 mL, 37% in water) at 0° C. was added sodium nitrite (32.2 g, 469 mmol, in 100 mL water) dropwise. The mixture was stirred for 1 h at which time, potassium iodide (82.0 g, 490 mmol, in 100 mL H2O) was added dropwise. The mixture was stirred at rt for 2 h and then extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and purified by flash chromatography to provide the title compound (98.6 g, 368 mmol, 83%). 1H NMR (400 MHz, CDCl3) δ ppm 7.15-7.23 (m, 1H), 7.75 (dd, J=3.50 Hz, J=7.60 Hz, 1H), 7.97 (dd, J=1.6 Hz, J=8.8 Hz, 1H).

Workup

  1. additionwas added dropwise
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-69b61a457d2042898627f7be6e3f41d0
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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