Acetonitrile → HCID 65100407, compound

HRID 1620819Notes

Reaction equation

HRID 1620819 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O)=[O:9].C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:7][C:4]1[S:5][CH:6]=[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:8]=[O:9])[CH:3]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 6385844-Bromo-2-methylthiophene

Product 1

HCID 65100407HCID 65100407, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, 4-bromo-2-methyl-thiophene (653 mg, 3.69 mmol), 2-formyl phenylboronic acid (500 mg, 3.36 mmol) and 7 ml of actonitrile were mixed. 6.7 ml of 1N aqueous sodium carbonate was added to above solution, followed by 5 mole percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150° C. for 5 minutes with microwave irradiation. After cooling, 50 ml of ethyl acetate was added, the organic layer was separated, washed with water, dried with sodium sulfate, the organic solvent was evaporated and the residue was purified by ISCO to give 550 mg of 2-(5-methyl-thiophen-3-yl)benzaldehyde, yield 81%.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried with sodium sulfate
  6. customthe organic solvent was evaporated
  7. customthe residue was purified by ISCO

Sources & evidence

ORD record
ord-ab2f932493bf4975a6fb56a020aad7be
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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