Potassium Iodide → 3-Fluoro-2-iodobenzoic acid

HRID 1868830Notes

Reaction equation

HRID 1868830 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[I-:16].[K+]>O.CS(C)=O.OS(O)(=O)=O>[F:15][C:14]1[C:6]([I:16])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 3

HCID 4875Potassium IodideHCID 5864082-Amino-3-fluorobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 223203083-Fluoro-2-iodobenzoic acidYield 87.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (6.7 g, 97 mmol) in water (25 mL) was added to a solution of 2-amino-3-fluorobenzoic acid (10.0 g, 64 mmol) in DMSO (25 mL) and 30% H2SO4 (75 mL) at 0° C. The mixture was stirred for 1 hour at 0° C. and then potassium iodide (27 g, 161 mmol) was added dropwise as a solution in water (25 mL). The ice bath was removed and the mixture was stirred at room temperature for 4 hours, and then partitioned between EtOAc and 2M sodium sulfite. The layers were mixed, separated, and the organic layer was washed with 2M sodium sulfite once and brine once, dried over anhydrous MgSO4, and concentrated in vacuo to give 14.90 g of a yellow solid. MS m/e=265 (M−H)+.

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. custompartitioned between EtOAc and 2M sodium sulfite
  4. additionThe layers were mixed
  5. customseparated
  6. washthe organic layer was washed with 2M sodium sulfite once
  7. dry with materialbrine once, dried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5875fbf1ee54bb4972ea0427e68bf1b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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