Sodium Iodide → HCID 86627412, compound

HRID 1686147Notes

Reaction equation

HRID 1686147 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16]Br)[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CC(C)=O>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86627413HCID 86627413, compound

Product 1

HCID 86627412HCID 86627412, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2-Bromobenzyloxy)-4-(2-bromoethoxy)benzaldehyde (100 mg, 0.241 mmol) synthesized in step 3 was dissolved in acetone, and K2CO3 (66.6 mg, 0.482 mmol), NaI (3.6 mg, 0.024 mmol), and morpholine (0.032 ml, 0.362 mmol) were added to the solution, followed by flux with stirring. After stirring for 24 hours, the solution was cooled, filtered, washed with brine, and extracted with CH2Cl2. Then, the extract was dried over anhydrous MgSO4 and filtered and the filtrate was concentrated in a vacuum. The residue was subjected to column chromatography (50% EA/Hx) to afford the object compound (yellowish oil, 52 mg, 51%).

Workup

  1. stirringAfter stirring for 24 hours
  2. temperaturethe solution was cooled
  3. filtrationfiltered
  4. washwashed with brine
  5. extractionextracted with CH2Cl2
  6. dry with materialThen, the extract was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in a vacuum
  9. customto afford the object compound (yellowish oil, 52 mg, 51%)

Sources & evidence

ORD record
ord-b019cecfd7704f389d6759c97aee35cb
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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