Sodium Carbonate → [2,2'-Bithiophene]-5-carboxaldehyde

HRID 363521Notes

Reaction equation

HRID 363521 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.C([C:24]1[S:28][C:27]([CH:29]=[O:30])=[CH:26][CH:25]=1)(O)=O>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:24]1[S:28][C:27]([CH:29]=[O:30])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 8188825-Formyl-2-thiophenecarboxylic AcidHCID 27339602-Thiopheneboronic acid

Product 1

HCID 364428[2,2'-Bithiophene]-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a solution of thien-2-ylboronic acid (0.939 g, 7.34 mmol) and Na2CO3 (2.40 g, 22.6 mmol) in water (75 mL) is added p-dioxane (75 mL). This mixture is treated sequentially with 5-carboxy-2-thiophenecarboxaldehyde (1.43 g, 7.48 mmol) and palladium (II) acetate (151 mg, 0.673 mmol) and allowed to stir at ambient temperature for 16 hours. The solvent is evaporated in vacuo. To the residue is added EtOAc (400 mL) and water (300 mL). The aqueous layer is acidified to pH 1 with 1.0N aq. HCl. The aqueous layer is extracted with EtOAc (2×200 mL). The organic extracts are combined, washing with brine (200 mL), 5% aq. Na2S2O3 (200 mL), sat. aq. NaCl (200 mL), drying (Na2SO4), and the solvent evaporation in vacuo affords the title compound.

Workup

  1. customThe solvent is evaporated in vacuo
  2. additionTo the residue is added EtOAc (400 mL) and water (300 mL)
  3. extractionThe aqueous layer is extracted with EtOAc (2×200 mL)
  4. washwashing with brine (200 mL), 5% aq. Na2S2O3 (200 mL), sat. aq. NaCl (200 mL)
  5. dry with materialdrying (Na2SO4)
  6. customthe solvent evaporation in vacuo

Sources & evidence

ORD record
ord-e97527c8980b4262893c7b5db2e97ea9
Source dataset
uspto-grants-1999_02
Patent number
US05874452

Reaction notes

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