Sodium Bicarbonate → HCID 13354808, compound

HRID 1836680Notes

Reaction equation

HRID 1836680 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.C(=O)(O)[O-].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 13354808HCID 13354808, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirring solution of 3-bromo-thiophene-2-carbaldehyde (0.120 g, 0.6 mmol)and 2thiopheneboronic acid (0.134 g, 0.75 mmol) in 1,2-dimethoxyethane(4.0 ml) under argon was added sodium bicarbonate solution (1.0 M, 3.0 ml). Tetrakis(triphenylphosphine) palladium (0) (0.022 g, 0.02 mmol) was then added to the reaction mixture. The solution was heated under reflux for 24 hrs, then was extracted with ethyl acetate three times. The combined organic layers were dried over MgSO4. The solvent was evaporated to yield [2,3′]bithiophenyl-2′-carbaldehyde as a colorless oil which was used directly in next step, without further purification.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 24 hrs
  3. extractionwas extracted with ethyl acetate three times
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2b481b45b8ee4e6a8d8eaa981c0ea398
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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