Iodine → HCID 68615191, compound

HRID 1712195Notes

Reaction equation

HRID 1712195 reaction equation
C1CCCCC1.C([Li])(CC)C.[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH:16]=[CH:17][CH:18]=1.[I:31]I>O.C1COCC1>[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH:16]=[CH:17][C:18]=1[I:31]

Participants

7

Reactant 4

HCID 807IodineHCID 8078CyclohexaneHCID 686168432-[2-(3-Fluorophenyl)ethyl]naphthaleneHCID 178418400CID 53628100

Product 1

HCID 68615191HCID 68615191, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 53.35 ml cyclohexane solution of sec-butyl lithium in a concentration of 1.01M was dropped into a 200 ml THF solution of 8.43 g (33.68 mmol) of the above 2-[2-(3-fluorophenyl)ethyl]naphthalene at −70° C. After the dropping was finished, the reaction solution was stirred at the same temperature for 1 hour, added with a 200 ml THF solution of 13.68 g (=53.90 mmol) of iodine through dropping and then slowly heated to room temperature. After being stirred for 18 hours, the reaction solution was added in iced water dissolved with Na2S2O3.5H2O, and then the reaction mixture was extracted twice with toluene. The extract was washed thrice with water, and was then dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained orange solid of 13.05 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent to obtain a yellowish solid of 11.66 g, which was recrystallized with a mixed solvent of Solumix/heptane in a ratio of 5:1 to obtain 10.60 g of 2-[2-(3-fluoro-4-iodophenyl)ethyl]naphthalene as yellowish crystals.

Workup

  1. stirringAfter being stirred for 18 hours
  2. extractionthe reaction mixture was extracted twice with toluene
  3. washThe extract was washed thrice with water
  4. dry with materialwas then dried with anhydrous MgSO4
  5. customAfter the solvent was evaporated under a reduced pressure
  6. customthe obtained orange solid of 13.05 g was purified with silica gel chromatography
  7. customto obtain a yellowish solid of 11.66 g, which
  8. customwas recrystallized with a mixed solvent of Solumix/heptane in a ratio of 5:1

Sources & evidence

ORD record
ord-9e1372f4bae74b74afad5c5819c471a3
Source dataset
uspto-grants-2010_09
Patent number
US07790915B2

Reaction notes

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