Acetonitrile → 2-(4-Methylthiophen-3-yl)benzaldehyde

HRID 1988007Notes

Reaction equation

HRID 1988007 reaction equation
Br[C:2]1[C:6]([CH3:7])=[CH:5][S:4][CH:3]=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:6]1[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:8]=[O:9])=[CH:3][S:4][CH:5]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 27349353-Bromo-4-methylthiophene

Product 1

HCID 866210832-(4-Methylthiophen-3-yl)benzaldehydeYield 78%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, 3-bromo-4-methyl-thiophene (653 mg, 3.69 mmol), 2-formyl phenylboronic acid (500 mg, 3.36 mmol) and 7 ml of actonitrile were mixed together. 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 to give crude product, which was purified by ISCO CombiFlash column to give 530 mg of 2-(4-methyl-thiophen-3-yl)benzaldehyde, yield: 78%.

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. customto give crude product, which
  8. customwas purified by ISCO CombiFlash column

Sources & evidence

ORD record
ord-df27bbce172f4295beda4a1a09e09ee8
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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