Iodine → HCID 19081622, compound

HRID 963407Notes

Reaction equation

HRID 963407 reaction equation
CO[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16]OC)[CH:13]=2)[CH:8]=[CH:7][CH:6]=1.C([Li])CCC.[I:24]I.[Cl-].[NH4+]>C1COCC1.CCCCCC>[I:24][C:13]1[C:12]([O:15][CH3:16])=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]([O:4][CH3:3])=[CH:6][CH:7]=[CH:8]2

Participants

7

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 19081733HCID 19081733, compoundHCID 178418339Butyllithium

Product 1

HCID 19081622HCID 19081622, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

1.2 g of 1,7-bis-methoxymethoxy-naphthalene are dissolved in 9 ml of THF and cooled to -78°. 3.13 ml of a 1.6M n-butyl-lithium solution in hexane are added dropwise thereto and the mixture is stirred at room temperature overnight. Subsequently, it is again cooled to -78° and a solution of 1.25 g of iodine in 3.4 ml of THF is added dropwise. The mixture is warmed to room temperature and 10 ml of saturated ammonium chloride solution are added. The organic solvents are evaporated on a rotary evaporator and the residue is extracted three times with ether. After drying and evaporation the residue is chromatographed on silica gel with ethylene chloride. 0.72 g of 8-iodo-1,7-bis-methoxy-naphthalene is thus isolated. Yield: 40%. Mass spectrum: peaks inter alia at 374 (M+, 87%), 171 (40%), 45 (100%).

Workup

  1. temperaturecooled to -78°
  2. temperatureSubsequently, it is again cooled to -78°
  3. temperatureThe mixture is warmed to room temperature
  4. customThe organic solvents are evaporated on a rotary evaporator
  5. extractionthe residue is extracted three times with ether
  6. customAfter drying
  7. customevaporation the residue
  8. customis chromatographed on silica gel with ethylene chloride

Sources & evidence

ORD record
ord-5ba18431491144fc83405ee68caef838
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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