Sodium Carbonate → Benzaldehyde,2-benzo[b]thien-5-yl-

HRID 270012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270012
Br[C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O)=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[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:6]1[CH:7]=[CH:8][C:4]2[CH:3]=[C:2]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:11]=[O:12])[CH:10]=[CH:9][C:5]1=2

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 27765785-Bromo-1-benzothiophene

Produkt 1

HCID 60139760Benzaldehyde,2-benzo[b]thien-5-yl-Ausbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 5-Bromo-benzo[b]thiophene (compound PRE13) (3.68 g, 17.2 mmol) in toluene (183 mL) was added, under nitrogen, tetrakis(triphenylphosphine)-palladium (1.99 g, 1.72 mmol), then a solution of 2-formylphenylboronic acid (3.87 g, 25.8 mmol) in ethanol (20 mL) and at least dropwise aqueous sodium carbonate solution (3.64 g, 34.4 mmol) in water (20 mL). The reaction mixture was then heated to 80° C. for 3 h, cooled, concentrated, partitioned between ethyl acetate (120 mL) and water (70 mL) and acidified with hydrochloric acid (pH˜2). The organic layer was separated, dried over Na2SO4 and concentrated to give a crude residue that was purified by flash chromatography (silica, eluting solvent: (petroleum ether/AcOEt) 9.2/0.8) to give 3.31 g of compound PRE14 (orange yellow powder; yield=81%).

Aufarbeitung

  1. additionwas added, under nitrogen
  2. temperaturecooled
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate (120 mL) and water (70 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a crude residue that
  9. customwas purified by flash chromatography (silica, eluting solvent: (petroleum ether/AcOEt) 9.2/0.8)

Quellen und Nachweise

ORD-Eintrag
ord-7ee9c9f299ba4572b70062c261349b32
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449481B2

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