Iodine → Methyl 4-cyclobutyl-3-iodobenzoate

HRID 541285Notes

Reaction equation

HRID 541285 reaction equation
[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[I:15]([O-])(=O)(=O)=O.[Na+].II.S(=O)(=O)(O)O>C(O)(=O)C>[CH:1]1([C:5]2[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=2[I:15])[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 23667635Sodium periodateHCID 68288440Methyl 4-cyclobutylbenzoate

Product 1

HCID 68288885Methyl 4-cyclobutyl-3-iodobenzoateYield 101.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-cyclobutylbenzoate (168.1, 2.00 g, 10.5 mmol, 1.00 equiv) in acetic acid (30 mL) were carefully added sodium periodate (1.00 g, 4.68 mmol, 0.50 equiv), iodine (3.00 g, 11.8 mmol, 1.10 equiv) and sulfuric acid (0.15 g, 0.15 equiv). The resulting mixture was stirred overnight at 100° C. After cooling to room temperature, the reaction was then quenched by carefully adding 30 mL of Na2S2O3 (aq., sat.) and the resulting mixture was extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with 3×20 mL of brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield 1.50 g (45%) of the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was then quenched
  3. additionby carefully adding 30 mL of Na2S2O3 (aq., sat.)
  4. extractionthe resulting mixture was extracted with 3×20 mL of ethyl acetate
  5. washThe combined organic layers were washed with 3×20 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f9a937158e74a878390bcf4a2500e99
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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