Iodine → 4-Iodo-3-propyl-1H-isochromen-1-one

HRID 634402Notes

Reaction equation

HRID 634402 reaction equation
[C:1]([C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=[O:9])#[C:2][CH2:3][CH2:4][CH3:5].[I:16]I.C(=O)(O)[O-].[Na+]>C(#N)C.CCOCC>[I:16][C:1]1[C:6]2[C:7](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:8](=[O:10])[O:9][C:2]=1[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 10352815Methyl 2-(pent-1-ynyl)benzoate

Product 1

HCID 441304554-Iodo-3-propyl-1H-isochromen-1-oneYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl 2-(pent-1-ynyl)benzoate (intermediate C20.1, 3 g, 14.83 mmol), iodine (11.29 g, 44.5 mmol) and sodium bicarbonate (3.74 g, 44.5 mmol) were reacted in Acetonitrile (50 mL) for 20 min. at RT. The reaction mixture was diluted with Et2O and washed with 20% Na2S2O3aqueous and brine. The organic phase was then dried over Na2SO4 and concentrated under reduced pressure. The crude was dissolved in Et2O and purified over a silica pad to give the title compound (3.54 g, 76%) as a brown oil.

Workup

  1. washwashed with 20% Na2S2O3aqueous
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude was dissolved in Et2O
  5. custompurified over a silica pad

Sources & evidence

ORD record
ord-bda1468d4ce3499cb9ea081439db7cf4
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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