Iodine → Ethyl 4-(4-iodophenyl)bicyclo[2.2.2]octane-1-carboxylate

HRID 1670669Notes

Reaction equation

HRID 1670669 reaction equation
FC(F)(F)C(O[I:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)OC(=O)C(F)(F)F)=O.II.C1([C:30]23[CH2:37][CH2:36][C:33]([C:38]([O:40][CH2:41][CH3:42])=[O:39])([CH2:34][CH2:35]2)[CH2:32][CH2:31]3)C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[I:6][C:14]1[CH:15]=[CH:16][C:17]([C:30]23[CH2:37][CH2:36][C:33]([C:38]([O:40][CH2:41][CH3:42])=[O:39])([CH2:32][CH2:31]2)[CH2:34][CH2:35]3)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 21627803Ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 57991998Ethyl 4-(4-iodophenyl)bicyclo[2.2.2]octane-1-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[Bis(trifluoroacetoxy)iodo]benzene (3.78 g, 8.78 mmol) and iodine (1.061 g, 4.18 mmol) were added to a stirred solution of ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate (prepared according to the procedure described in WO 2007/071966) (2.16 g, 8.36 mmol, CAS 10207-26-8) in CHCl3 (50 mL). The resulting solution was stirred at ambient temperature for 90 minutes. The reaction mixture was poured into sodium thiosulfate (100 mL), extracted with DCM (2×100 mL), the organic layer was washed with aqueous sodium thiosulfate (2×80 mL), separated, dried over MgSO4, filtered and evaporated to afford a yellow oil which solidified on standing. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the title compound (2.78 g, 87%) as a white solid.

Workup

  1. customprepared
  2. extractionextracted with DCM (2×100 mL)
  3. washthe organic layer was washed with aqueous sodium thiosulfate (2×80 mL)
  4. customseparated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a yellow oil which
  9. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  10. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-3288bfae3f49455fb376c96898be6d83
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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