Sodium Carbonate → 2,4-Difluoro-5-iodobenzoic acid

HRID 1670792

Reaction equation

HRID 1670792 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 741022,4-Difluorobenzoic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 111297952,4-Difluoro-5-iodobenzoic acidYield 94.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2,4-Difluorobenzoic acid 10 (45.0 g, 285 mmol) was dissolved in concentrated sulfuric acid (360 mL) at 0° C. and N-iodosuccinimide (NIS, 64 g, 284 mmol) was added in portions at 0° C. The mixture was allowed to warm to room temperature (rt) and stirred 4 hours (h). The mixture was poured into ice water (approximately 1000 mL) and 10% aqueous sodium carbonate solution (80 mL) was added. After the mixture was stirred for 0.5 h, the precipitate was filtered, washed with water (approximately 2000 mL), then dried at 50° C. in a convection oven for 2 days to provide 76.3 g (94%) of 11 as a gray solid.

Workup

  1. additionwas added
  2. stirringAfter the mixture was stirred for 0.5 h
  3. filtrationthe precipitate was filtered
  4. washwashed with water (approximately 2000 mL)
  5. customdried at 50° C. in a convection oven for 2 days

Sources & evidence

ORD record
ord-15bacb8cd0ea4af5b43b066be6af321f
Source dataset
uspto-grants-2011_08
Patent number
US07994194B2

Linked notes

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