Iodine → HCID 21449903, compound

HRID 596458Notes

Reaction equation

HRID 596458 reaction equation
[Mg].II.BrC(Br)C.[CH2:8]([C:13]1[CH:26]=[CH:25][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)[C:9]([CH3:12])([CH3:11])[CH3:10].[N:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][CH:28]=1.[Cl-].[NH4+]>CCOCC.O1CCCC1>[CH2:8]([C:13]1[CH:26]=[CH:25][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:33]([C:30]3[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=3)[OH:34])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

9

Reactant 6

HCID 807IodineHCID 112011,1-DibromoethaneHCID 133894-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 21449910HCID 21449910, compound

Product 1

HCID 21449903HCID 21449903, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To form a Grignard reagent, to 3.6 g. of magnesium metal and a crystal of iodine are added, all at once, 25 ml. of a solution of 9.0 g. dibromoethane and 25.0 g. of p-(4-neopentylphenoxy)-bromobenzene in 150 ml. of absolute tetrahydrofuran (THF). After initiating the Grignard reaction, the rest of the above THF solution is added dropwise to maintain gentle reflux. The (Grignard reagent) reaction mixture is thereafter refluxed for half an hour; cooled and to it is added, dropwise, a solution of 8.3 g. of 4-pyridine-carboxaldehyde in 20 ml. of absolute THF. The reaction mixture is then stirred overnight, decomposed with saturated ammonium chloride aqueous solution and 100 ml. ether added. The organic phase is separated, dried over anhydrous sodium sulfate, filtered, and evaporated under vacuum to dryness to yield a residue. The residue is chromatographed on silica gel, first with toluene as the eluent and subsequently with toluene containing increasing concentrations of chloroform. The desired fractions are collected and evaporated under vacuum to dryness to yield a residue. From the residue is crystallized (from ether) the title product, m.p. 120°-122° C.

Workup

  1. customthe Grignard reaction
  2. temperatureto maintain gentle reflux
  3. temperatureis thereafter refluxed for half an hour
  4. temperaturecooled and to it
  5. additionis added
  6. customThe organic phase is separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum to dryness
  10. customto yield a residue
  11. customThe residue is chromatographed on silica gel, first with toluene as the eluent and subsequently with toluene containing
  12. temperatureincreasing concentrations of chloroform
  13. customThe desired fractions are collected
  14. customevaporated under vacuum to dryness
  15. customto yield a residue
  16. customFrom the residue is crystallized (from ether) the title product, m.p. 120°-122° C.

Sources & evidence

ORD record
ord-c36032ff241c4c519e8a7e55336ffd05
Source dataset
uspto-grants-1977_03
Patent number
US04011232

Reaction notes

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