Acetic Acid → HCID 68901947, compound

HRID 1987701Notes

Reaction equation

HRID 1987701 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)([O-:3])=[O:2].[I:15]N1C(=O)CCC1=O.C(O)(=O)C>CO>[I:15][C:12]1[S:11][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 91672612-(2-nitrophenyl)thiophene

Product 1

HCID 68901947HCID 68901947, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-nitro-phenyl)-thiophene (23 g, 0.11 mol) and N-iodosuccinimide (37 g, 0.165 mol) were dissolved in 110 ml of methanol. To this solution, acetic acid (10 g, 0.165 mol) was added. After stirring the reaction mixture for 4 hours at room temperature, the solvent was evaporated. The remainder was taken up in a mixture of ice and water and extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and evaporated, delivering 2-iodo-5-(2-nitro-phenyl)-thiophene (28 g).

Workup

  1. customthe solvent was evaporated
  2. additionThe remainder was taken up in a mixture of ice and water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-abb13ff22a104882a68ed815deb540ba
Source dataset
uspto-grants-2009_06
Patent number
US07553798B2

Reaction notes

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