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

HRID 1820269Notes

Reaction equation

HRID 1820269 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-11c6f7e1262d4f7bb2d038828a9d0217
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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