Sodium Sulfite → 2,3-Difluoro-5-iodobenzoic acid

HRID 491519Notes

Reaction equation

HRID 491519 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>FC(F)(F)S(O)(=O)=O>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 108913672,3-Difluoro-5-iodobenzoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

2,3-Difluorobenzoic acid (5.0 g, 31.6 mmol) was dissolved in trifluoromethanesulfonic acid (25 ml) and N-iodosuccinimide (8.55 g, 38.0 mmol) was cast by portions under an argon stream at 0° C. After stirring at room temperature for 3 hr, the reaction mixture was poured into sodium sulfite in ice water and stirred. The precipitated solid was collected by filtration, washed with water, and vacuum dried to give the object product (7.5 g, yield 84%) as a pale-pink solid.

Workup

  1. customat 0° C
  2. stirringstirred
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water, and vacuum
  5. customdried

Sources & evidence

ORD record
ord-d381f946179a477fa8cbf2c39e18338b
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Reaction notes

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