Iodine → Methyl 5-iodothiophene-2-carboxylate

HRID 1876914Notes

Reaction equation

HRID 1876914 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].II.FC(F)(F)C(O[I:17](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[I:17][C:5]1[S:1][C:2]([C:6]([O:8][CH3:9])=[O:7])=[CH:3][CH:4]=1

Participants

8

Reactant 5

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 79340Methyl thenoateHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 13156399Methyl 5-iodothiophene-2-carboxylateYield 90.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl thiophene-2-carboxylate (0.46 mL, 4 mmol) in anhydrous methylene chloride (5 mL) was added iodine (510 mg, 2 mmol) followed by [bis(trifluoroacetoxy)iodo]benzene (900 mg, 2.1 mmol). The reaction mixture was stirred at RT for 1.5 hr before saturated aqueous sodium bicarbonate solution (10 mL) and saturated aqueous sodium thiosulfate solution (2 mL) were added. The mixture was then stirred at RT for 20 min. The aqueous layer was separated and extracted with methylene chloride (2×1 mL). The combined organic solutions were dried (Na2SO4). Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave methyl 5-iodothiophene-2-carboxylate (500 mg, 1.9 mmol, 47% yield) as a solid.

Workup

  1. additionwere added
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride (2×1 mL)
  4. dry with materialThe combined organic solutions were dried (Na2SO4)

Sources & evidence

ORD record
ord-1bf6ee4dc11545b6be1b5670c83ac4fa
Source dataset
uspto-grants-2012_11
Patent number
US08309730B2

Reaction notes

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