Iodine → HCID 54757833, compound

HRID 2042998Notes

Reaction equation

HRID 2042998 reaction equation
OS(O)(=O)=O.[C:6]1([C@@H:12]2[CH2:14][C@H:13]2[C:15]([OH:17])=[O:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I:18]I>O.CC(O)=O>[I:18][C:9]1[CH:10]=[CH:11][C:6]([C@@H:12]2[CH2:14][C@H:13]2[C:15]([OH:17])=[O:16])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 237413trans-2-Phenylcyclopropanecarboxylic acid

Product 1

HCID 54757833HCID 54757833, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of H2SO4 (0.1 mL) in water (1 mL) and AcOH (4 mL) in a 25 mL flask was added trans-2-phenylcyclopropanecarboxylic acid (200 mg, 1.23 mmol), iodine (173 mg, 0.68 mmol) and KIO3 (61 mg, 0.28 mmol). The reaction mixture was heated to reflux, and added AcOH (6 mL) in portions of 2 mL to rinse iodine down the condenser. After 4 hours, when no further color changes appeared, the reaction was cooled to room temperature, quenched with 1M Na2S2O4 and added water. The mixture was extracted with EtOAc (3×), and the combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum. The crude product containing minor impurities of starting material and the ortho-iodinated product, was recrystallized from PE to provide 157 mg (44%) trans-2-(4-iodophenyl)cyclopropanecarboxylic acid as a pure and white crystalline product: Rt=11.33 min (HPLC method I); 1H NMR (CDCl3) δ 7.62-7.58 (m, 2H), 6.87-6.84 (m, 2H), 2.56-2.51 (m, 1H), 1.89-1.84 (m, 1H), 1.69-1.64 (m, 1H), 1.39-1.34 (m, 1H); 13C NMR (CDCl3) δ 179.3, 139.2, 137.6, 128.3, 91.7, 26.5, 23.9, 17.4; ESI-MS m/z 311.0 (M+Na+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. washto rinse iodine down the condenser
  4. customquenched with 1M Na2S2O4
  5. additionadded water
  6. extractionThe mixture was extracted with EtOAc (3×)
  7. washthe combined extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under vacuum
  10. additionThe crude product containing minor impurities of starting material
  11. customthe ortho-iodinated product, was recrystallized from PE

Sources & evidence

ORD record
ord-1c4f539c3a5149d79d38cd8b89281915
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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