Sodium Iodide → Methyl 5-iodo-1-benzothiophene-2-carboxylate

HRID 734829Notes

Reaction equation

HRID 734829 reaction equation
[Na+].[I-:2].CNCCNC.Br[C:10]1[CH:22]=[CH:21][C:13]2[S:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:12]=2[CH:11]=1>O1CCOCC1.[Cu]I>[I:2][C:10]1[CH:22]=[CH:21][C:13]2[S:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 2824065methyl 5-bromo-1-benzothiophene-2-carboxylate

Product 1

HCID 19007488Methyl 5-iodo-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Under an argon atmosphere 0.35 g (1.84 mmol) of CuI, 5.53 g (36.88 mmol) of NaI, and 0.39 mL (3.67 mmol) of N,N′-dimethylethylenediamine were added to a solution of 5.0 g (18.4 mmol) of methyl 5-bromobenzo[b]thiophen-2-carboxylate in 18 mL of 1,4-dioxane and after rinsing again with argon the reaction mixture was heated overnight to 110° C. After cooling, the reaction mixture was combined with 30% aqueous ammonia and water, exhaustively extracted with EtOAc, and the combined organic phases were twice washed with water and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was triturated with DIPE and MTBE, suction filtered, and dried in the air. Yield: 3.4 g (58% of theoretical); C10H7IO2S (M=318.132); calc.: molpeak (M)+: 318; found: molpeak (M)+: 318; HPLC-MS: 6.4 minutes (method B).

Workup

  1. washafter rinsing again with argon the reaction mixture
  2. temperaturewas heated overnight to 110° C
  3. temperatureAfter cooling
  4. extractionexhaustively extracted with EtOAc
  5. washthe combined organic phases were twice washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe residue was triturated with DIPE and MTBE, suction
  8. filtrationfiltered
  9. customdried in the air
  10. custom6.4 minutes (method B)

Sources & evidence

ORD record
ord-8892842ff68248538887fefcbb5ecb77
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

Loading…