Water → Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate

HRID 2288060Notes

Reaction equation

HRID 2288060 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:14]([C:16]1[S:20][C:19]2[CH:21]=[CH:22][C:23](I)=[CH:24][C:18]=2[CH:17]=1)#[N:15].O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][C:23]1[CH:22]=[CH:21][C:19]2[S:20][C:16]([C:14]#[N:15])=[CH:17][C:18]=2[CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 187029595-Iodobenzo[b]thiophene-2-carbonitrile

Product 1

HCID 54151697Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylateYield 61%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Methyl acrylate (2 g), triethylamine (2.35 g) and palladium acetate (0.05 g) was added to 2-cyano-5-iodobenzo[b]thiophene (4.8 g) in DMF (25 ml) and the mixture was stirred under argon at 90° C. for 30 minutes. The mixture was allowed to cool and then added to water (50 ml). The solid which precipitated was collected by filtration and dissolved in chloroform. Activated charcoal was added and the mixture filtered and the filtrate dried (MgSO4). Solvent was removed by evaporation to give methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate (2.5 g); NMR (d6 -DMSO): 3.75 (s, 3H), 6.7 (d, 1H), 7.8 (d, 1H), 8.0 (dd, 1H), 8.2 (d, 1H), 8.3 (d, 1H), 8.85 (s, 1H).

Workup

  1. temperatureto cool
  2. customThe solid which precipitated
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in chloroform
  5. additionActivated charcoal was added
  6. filtrationthe mixture filtered
  7. dry with materialthe filtrate dried (MgSO4)
  8. customSolvent was removed by evaporation

Sources & evidence

ORD record
ord-e892c006547f43a9b921d7adfb79c264
Source dataset
uspto-grants-2000_07
Patent number
US06087336

Reaction notes

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