N-bromobutanimide → 3-Bromo-7-(4-methylbenzyl)-1-benzothiophene

HRID 909814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909814
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:15]3[S:14][CH:13]=[CH:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:17][CH:16]=3)[C:15]=2[S:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 670691007-(4-Methylbenzyl)benzo[b]thiophene

Produkt 1

HCID 670690913-Bromo-7-(4-methylbenzyl)-1-benzothiopheneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

An acetonitrile (30 mL) solution of 7-(4-methylbenzyl)-1-benzothiophene (1.24 g, 5.20 mmol) was added with N-bromosuccinimide (1.01 g, 5.72 mmol) and stirred at room temperature for two hours. The solvent was evaporated under reduced pressure and diluted with ethyl acetate. After washed with 20 wt % sodium thiosulfate aqueous solution and brine, the organic phase was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=100:1-50:1) to obtain a colorless powdered title compound (0.92 g, 56%).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washAfter washed with 20 wt % sodium thiosulfate aqueous solution and brine
  4. dry with materialthe organic phase was dried with anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained
  7. customby evaporating the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=100:1-50:1)

Quellen und Nachweise

ORD-Eintrag
ord-c843dfb426f6449ca4d7e941f4cfb55c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017792B2

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