Sodium Carbonate → 2-(3-Methoxyphenyl)-6,7-dihydro-5H-benzo[b]thiophen-4-one

HRID 643732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643732
Br[C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.B(O)O.[CH3:15][O:16][C:17]1[CH:18]=[C:19](O)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].CCO.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=3[CH:3]=2)[CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 6160702-Bromo-4,5,6,7-tetrahydro-1-benzothiophen-4-oneHCID 19096565Water ethanolHCID 178491272HCID 178491272, Verbindung

Produkt 1

HCID 592628582-(3-Methoxyphenyl)-6,7-dihydro-5H-benzo[b]thiophen-4-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To 2-bromo-6,7-dihydro-5H-benzo[b]thiophen-4-one (5 g, 21.74 mmol) was successively added 3-methoxyphenol boronic acid (3.63 g, 23.92 mmol), 2M Na2CO3(aq) (43.5 mL, 86.98 mmol), Pd(PPh3)4 (251mg, 0.22 mmol), 3:4 EtOH/H2O (37.5 mL) and DME (62.5 mL). The reaction mixture was degassed and heated to reflux for 12 hours. EtOAc (250 mL) was added and the crude reaction mixture was washed with water (2×100 mL). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with EtOAc:hexanes (20:80) to give the title compound as an off-white solid in 95% yield. MS (ES+) 259. δH (d6 DMSO) 2.13 (2H, quint.), 2.50 (2H, m), 3.05 (2H, t), 3.81 (3H, s), 6.91 (1H, m), 7.20-7.22 (2H, m), 7.34 (1H, m), 7.67 (1H, s).

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. temperatureheated
  3. temperatureto reflux for 12 hours
  4. additionEtOAc (250 mL) was added
  5. customthe crude reaction mixture
  6. washwas washed with water (2×100 mL)
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with EtOAc:hexanes (20:80)

Quellen und Nachweise

ORD-Eintrag
ord-55a137c968b5499b8ef3005f8b13e7ae
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700609B2

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