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

HRID 2282106Notes

Reaction equation

HRID 2282106 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, stirred for 10 minutes followed by 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, d1-chloroform) δ: 4.45 (q, 2H), 3.38 (s, 3H), 1.43 (t, 3H).

Workup

  1. stirringstirred 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-f05113747b244bbc8d6b00ab23280c19
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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