Iodine → 3-Iodo-4-(propan-2-yl)benzoic acid

HRID 1016199Notes

Reaction equation

HRID 1016199 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.[I:18]I>O>[I:18][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[CH:1]([CH3:3])[CH3:2])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 108204-Isopropylbenzoic Acid

Product 1

HCID 448285203-Iodo-4-(propan-2-yl)benzoic acidYield 0.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Isopropylbenzoic acid (4.26 g, 25.9 mmol), sulfuric acid (25 mL), and water (2 mL) was heated to 95° C. and iodine (14.42 g, 56.8 mmol) was slowly added portionwise. The reaction was maintained at this temperature for 48 h. The reaction was cooled, poured into ice and extracted with methylene chloride. The organic extracts were dried over sodium sulfate, filtered, concentrated and then purified by reverse phase HPLC (MeOH/water/TFA) to yield 3-iodo-4-isopropylbenzoic acid (60 mg).

Workup

  1. temperatureThe reaction was maintained at this temperature for 48 h
  2. temperatureThe reaction was cooled
  3. additionpoured into ice
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by reverse phase HPLC (MeOH/water/TFA)

Sources & evidence

ORD record
ord-0dc83b2f84d743a6a335b5e4d10fc601
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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