Iodine → 2-Iodo-6-methoxynaphthalene

HRID 1194507Notes

Reaction equation

HRID 1194507 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2.C([Li])(C)(C)C.[I:19]I.O>C1COCC1>[I:19][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418306HCID 178418306, compound

Product 1

HCID 3490672-Iodo-6-methoxynaphthaleneYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.00 g (4.22 mmol, Aldrich) of 6-bromo-2-methoxynaphthalene in 10 ml of dry THF at -78° was added dropwise 4.5 ml (1.4M in pentane, 6.3 mmol, Aldrich) of t-butyllithium solution over 10 minutes. The reaction mixture was stirred at -78° for 30 minutes then at 0° for 15 minutes. The resulting yellow solution was re-cooled to 31 78° then 1.20 g (4.72 mmol, Aldrich) of iodine was added in one portion. The reaction mixture was warmed to room temperature, stirred for 1 hour then added to 50 ml of H2O and extracted with 50 ml of ethyl acetate. The organic extract was washed with an additional 50 ml of H2O, dried (MgSO4) and concentrated in vacuo to give a solid. The crude solid was recrystallized (EtOAc/petroleum ether) to afford 805 mg (67%) of title compound as pale yellow flakes, m.p. 142°-143°.

Workup

  1. waitat 0° for 15 minutes
  2. temperatureThe resulting yellow solution was re-cooled to 31 78°
  3. stirringstirred for 1 hour
  4. extractionextracted with 50 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with an additional 50 ml of H2O
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a solid
  10. customThe crude solid was recrystallized (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-ee8b9dfa7a6c445e84a7dda10b1c066e
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Reaction notes

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