3-Fluoro-p-toluic acid → 3-Fluoro-5-iodo-4-methylbenzoic acid

HRID 1619135Notes

Reaction equation

HRID 1619135 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([OH:15])=[O:14]>FC(F)(F)S(O)(=O)=O>[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([I:1])[C:18]=1[CH3:19])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 676873-Fluoro-p-toluic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 444794453-Fluoro-5-iodo-4-methylbenzoic acidYield 83.8%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

N-Iodosuccinimide (3.31 g, 14.7 mmol) was added in portions over a 3-hour period to a stirred solution of 3-fluoro-4-methylbenzoic acid (2.27 g, 14.7 mmol) in trifluoromethanesulphonic acid (15 mL) at 0° C. The mixture was warmed to room temperature, stirred overnight and then poured into an ice-water mixture and the precipitate that formed was collected by filtration and washed with water. The solid was dissolved in ethyl acetate, washed with aqueous sodium thiosulphate and brine, dried (MgSO4) and dried to give the title compound (3.45 g, 59%) as a solid.

Workup

  1. customthe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. washwashed with aqueous sodium thiosulphate and brine
  6. dry with materialdried (MgSO4)
  7. customdried

Sources & evidence

ORD record
ord-3dc00ffef59a4c188276760e98b65348
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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