Potassium Carbonate → Ethyl 4-cyano-3-iodo-5-(methylsulfonyl)thiophene-2-carboxylate

HRID 2401708Notes

Reaction equation

HRID 2401708 reaction equation
[C:1]([C:3]1[C:4]([I:15])=[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:6][C:7]=1SC)#[N:2].[CH:16]1C=C(Cl)C=C(C(OO)=O)C=1.[S:27]([O-:30])([O-])=[O:28].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C1COCC1>[I:15][C:4]1[C:3]([C:1]#[N:2])=[C:7]([S:27]([CH3:16])(=[O:30])=[O:28])[S:6][C:5]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 40152061Ethyl 4-cyano-3-iodo-5-(methylthio)thiophene-2-carboxylate

Product 1

HCID 40152062Ethyl 4-cyano-3-iodo-5-(methylsulfonyl)thiophene-2-carboxylateYield 86.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-cyano-3-iodo-5-(methylsulfanyl)thiophene-2-carboxylate (7.2 g, 20.4 mmol) was dissolved in DCM (200 mL) and THF (100 mL) and m-CPBA (9.14 g, 40.8 mmol) was added. The reaction mixture was stirred at rt overnight. Sodium sulfite (5.14 g, 40.8 mmol) was added and the mixture was stirred for 10 minutes followed by the addition of potassium carbonate (8.45, 61.2 mmol). The suspension was stirred at rt for 1 hour and filtered through celite, washed with DCM and the solvent was evaporated to afford ethyl 3-iodo-4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate (6.80 g, 78%). LCMS: (FA) ES+ 386. 1H NMR (400 MHz, CDCl3) δ: 4.45 (q, 2H), 3.38 (s, 3H), 1.43 (t, 3H).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. stirringThe suspension was stirred at rt for 1 hour
  3. filtrationfiltered through celite
  4. washwashed with DCM
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8af9c860ee3b497ea75e395eec9f225e
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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