Sodium Carbonate → 2-(Thiophen-2-yl)benzaldehyde

HRID 1836678Notes

Reaction equation

HRID 1836678 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O>COCCOC>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 27339602-Thiopheneboronic acid

Product 1

HCID 27955582-(Thiophen-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 2-bromobenzaldehyde (1.17 mL, 10.0 mmol) and 2.0 M aqueous sodium carbonate (75 mL) in DME (225 mL) were added thiophene-2-boronic acid (1.53 g, 12.0 mmol) and tetrakis(triphenylphosphine)palladium[0] (578 mg, 0.5 mmol). The mixture was heated to reflux under nitrogen for 16 hr. The resulting solution was cooled, and the crude product was extracted from aqueous solution with ethyl acetate. The organic layer was dried over MgSO4, and the solvents were removed under vacuum. The crude product was purified on flash column with 25% DCM in hexane to yield 2-(2-thienyl)benzaldehyde.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 16 hr
  3. temperatureThe resulting solution was cooled
  4. extractionthe crude product was extracted from aqueous solution with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvents were removed under vacuum
  7. customThe crude product was purified on flash column with 25% DCM in hexane

Sources & evidence

ORD record
ord-f864db07518b4978bae3c45030eddb1c
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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