Trifluoromethanesulfonic acid → 2,3-Difluoro-5-iodobenzoic acid

HRID 1168514Notes

Reaction equation

HRID 1168514 reaction equation
FC(F)(F)S(O)(=O)=O.[F:9][C:10]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].[I:20]N1C(=O)CCC1=O>>[F:9][C:10]1[C:18]([F:19])=[CH:17][C:16]([I:20])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 108913672,3-Difluoro-5-iodobenzoic acidYield 83%

Conditions

Temperature
2.5 °C

Procedure

A 500 mL, 3 neck round bottom flask, equipped with an overhead stirrer is charged with trifluoromethanesulfonic acid (100 g), cooled to 0-5° C. in an ice bath, and treated with 2,3-difluorobenzoic acid (18.96 g). To this mixture is added N-iodosuccinimide (32.4 g) portion-wise over a 10 min period. After an additional 3 min, the cooling bath is removed and the reaction mixture is allowed to warm to room temperature. After a total of 5 h, the reaction mixture is poured into 600 mL of vigorously stirred crushed ice/water containing 100 mL of 10% sodium sulfite solution. The beige colored precipitate is collected, washed with ice water and dried at 50° C. in a vacuum oven overnight to produce 28.2 g (83%) of the title compound. Physical characteristics: 1H NMR (CDCl3) δ10.35, 8.12, 7.76; MS (ESI−) m/z 283 (M−H)−.

Workup

  1. customA 500 mL, 3 neck round bottom flask, equipped with an overhead stirrer
  2. customthe cooling bath is removed
  3. temperatureto warm to room temperature
  4. additionAfter a total of 5 h, the reaction mixture is poured into 600 mL
  5. customcrushed ice/water containing 100 mL of 10% sodium sulfite solution
  6. customThe beige colored precipitate is collected
  7. washwashed with ice water
  8. customdried at 50° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-06f625162d7a4de4b3385998527cf13a
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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