Iodine → Methyl 4-cyclobutyl-3-iodobenzoate

HRID 1487851Notes

Reaction equation

HRID 1487851 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-cyclobutylbenzoate2×

Product 1

HCID 68288885Methyl 4-cyclobutyl-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-cyclobutylbenzoate (compound 9.1, 2.00 g, 10.5 mmol) in acetic acid (30 mL) was carefully added sodium periodate (1.00 g, 4.68 mmol), iodine (3.00 g, 11.8 mmol) and sulfuric acid (0.15 g). The resulting mixture was stirred overnight at 100° C. After cooling to room temperature, the reaction was then carefully quenched with saturated aqueous Na2S2O3 (30 mL) and the resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (3×20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield of the title compound as a yellow oil (1.50 g, 45%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was then carefully quenched with saturated aqueous Na2S2O3 (30 mL)
  3. extractionthe resulting mixture was extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic layers were washed with brine (3×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to yield of the title compound as a yellow oil (1.50 g, 45%)

Sources & evidence

ORD record
ord-4d775a79dca6473d9713ee5689e8386b
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…