Benzoic Acid → 3-Fluoro-5-iodo-4-methylbenzoic acid

HRID 2245044Notes

Reaction equation

HRID 2245044 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([I:17])C(=O)C1.F[C:19]([F:25])(F)S(O)(=O)=O>>[F:25][C:19]1[CH:3]=[C:2]([CH:7]=[C:6]([I:17])[C:5]=1[CH3:4])[C:1]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 62406Trifluoromethanesulfonic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 444794453-Fluoro-5-iodo-4-methylbenzoic acid

Conditions

Temperature
0 °C

Procedure

The benzoic acid (1.54 g, 0.01 mol) is dissolved in trifluoromethanesulfonic acid (10 mL) and cooled to about 0° C. NIS (2.25 g. 0.01 mol) is added in several portions over a 6 h period while maintaining the reaction temperature at about 0° C. The mixture is allowed to warm to rt. overnight. The reaction mixture is then poured over ice and extracted with ethyl acetate (3×). The organic layers are washed (Na2S2O5) and concentrated. The material is carried on crude.

Workup

  1. temperaturewhile maintaining the reaction temperature at about 0° C
  2. temperatureto warm to rt
  3. customovernight
  4. additionThe reaction mixture is then poured over ice
  5. extractionextracted with ethyl acetate (3×)
  6. washThe organic layers are washed (Na2S2O5)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-46489a370ca54d209d0597c4d881ac94
Source dataset
uspto-grants-2010_03
Patent number
US07678801B2

Reaction notes

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