Iodine → 2-Amino-3-fluoro-5-iodobenzoic acid

HRID 2234630Notes

Reaction equation

HRID 2234630 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].[I:17]I.S(=O)(O)[O-].[Na+]>O>[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 807IodineHCID 516892Sodium BicarbonateHCID 5864082-Amino-3-fluorobenzoic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 577314632-Amino-3-fluoro-5-iodobenzoic acidYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 999 mg (6.44 mmol) of 2-amino-3-fluorobenzoic acid in 35 mL of water was added 500 mg (5.95 mmol) of sodium bicarbonate. The reaction was stirred and 1.77 g (6.99 mmol) of iodine was slowly added. The reaction was stirred at room temperature for 48 hours. To the solution was added an aqueous solution of sodium bisulfite and the solution was stirred vigorously for 30 minutes. The precipitate was collected by vacuum filtration and washed with water. The brown solid was dried overnight to afford 1.14 g (4.06 mmol, 63% yield) of 2-amino-3-fluoro-5-iodo-benzoic acid. 1H NMR (500 MHz, DMSO-d6) δ 7.79 (t, 1H), 7.58 (dd, 1H).

Workup

  1. stirringThe reaction was stirred at room temperature for 48 hours
  2. stirringthe solution was stirred vigorously for 30 minutes
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with water
  5. customThe brown solid was dried overnight

Sources & evidence

ORD record
ord-f3e736818c964dad979f240d484d63f6
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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