Sodium Iodide → HCID 22347799, compound

HRID 2297570Notes

Reaction equation

HRID 2297570 reaction equation
FC1C=CC(C2C3C(=CC(C#N)=CC=3)CO2)=CC=1.Cl[CH2:20][CH2:21][CH2:22][C:23]1([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[C:31]2[C:26](=[CH:27][C:28]([C:32]#[N:33])=[CH:29][CH:30]=2)[CH2:25][O:24]1.[I-:41].[Na+]>CC(C)=O>[I:41][CH2:20][CH2:21][CH2:22][C:23]1([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[C:31]2[C:26](=[CH:27][C:28]([C:32]#[N:33])=[CH:29][CH:30]=2)[CH2:25][O:24]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 98561591-(4'-Fluorophenyl)-1,3-DihydroIsobenzofuran-5-CarbonitrileHCID 18382430HCID 18382430, compound

Product 1

HCID 22347799HCID 22347799, compoundYield 181%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-3-Iodopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (14a). A solution/suspension of 1-(3-chloropropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (20 g, 35 mmol, 80% pure) and sodium iodide (285 g, 1.9 mol) in dry acetone (200 ml) was heated at reflux for 24 h. The mixture was evaporated, and partitioned between ether and water. The ether layer was separated, and was washed successively with water and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated to give 1-(3-iodopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (25.8 g, 99%, 80% pure) as a thick oil. 1H NMR (CDCl3) δ 1.6-1.9 (m, 2H), 2.21 (ddd, 1H), 2.31 (ddd, 1H), 3.16 (td, 2H), 5.12 (dt, 1H), 5.21 (dt, 1H), 7.02 (t, 2H), 7.41 (d, 2H), 7.43 (d, 1H), 7.51 (s, 1H), 7.62 (dq, 1H)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe mixture was evaporated
  4. custompartitioned between ether and water
  5. customThe ether layer was separated
  6. washwas washed successively with water and brine
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-5ca89f954612406daab7845e2c900aab
Source dataset
uspto-grants-2002_12
Patent number
US06492374B2

Reaction notes

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