Dimethylformamide → Dibenzo(b,d)thiophene-2-carbaldehyde

HRID 594284

Reaktionsgleichung

Reaktionsgleichung von HRID 594284
Br[C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[Li]CCCC.CN([CH:23]=[O:24])C.[NH4+].[Cl-]>CCOCC>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:13]=[CH:14][C:2]=1[CH:23]=[O:24]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 2995082-BromodibenzothiopheneHCID 178418339Butyllithium

Produkt 1

HCID 641360Dibenzo(b,d)thiophene-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A cooled (0° C.) suspension of commercially available 2-bromodibenzo[b,d]thiophene (500 mg; 1.90 mmol) in anh. Et2O (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.26 ml; 2.01 mmol). The resulting suspension was further stirred at 0° C. for 30 min. Anh. DMF (0.156 ml; 2.03 mmol) was then added, and the mixture was stirred at rt for 20 min. Aq. sat. NH4Cl and Et2O were successively added, and the aq. layer was further extracted with Et2O. The mixed organic layers were washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM) afforded dibenzo[b,d]thiophene-2-carbaldehyde as an off-white solid. LC-MS (conditions A): tR=0.87 min.; no ionisation.

Aufarbeitung

  1. temperatureA cooled
  2. stirringthe mixture was stirred at rt for 20 min
  3. extractionthe aq. layer was further extracted with Et2O
  4. washThe mixed organic layers were washed with water
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM)

Quellen und Nachweise

ORD-Eintrag
ord-7ac324d6fe2c4573bcdca021ee6c52fc
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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