Bromine → N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamide

HRID 501526

Reaktionsgleichung

Reaktionsgleichung von HRID 501526
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][C:12](=[O:14])[CH3:13])[C:5]=2[O:4][CH2:3][CH2:2]1.[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:7]1[C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 658593N-(2,3-dihydro-1,4-benzodioxin-5-yl)acetamide

Produkt 1

HCID 23269228N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamideAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of compound 8C (0.80 g, 4.15 mmol) in chloroform (2.4 mL) cooled to −20° C. was slowly added a solution of bromine (0.22 mL, 4.35 mmol) in chloroform (1 mL) so that the reaction temperature was maintained below −10° C. The reaction was stirred at 0° C. for 5 min, and then quenched immediately with water. The mixture was extracted with CH2Cl2 (3×), the combined extracts washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with CH2Cl2 to afford the title compound (0.98 g).

Aufarbeitung

  1. temperaturewas maintained below −10° C
  2. customquenched immediately with water
  3. extractionThe mixture was extracted with CH2Cl2 (3×)
  4. washthe combined extracts washed with saturated NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (silica gel)
  9. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-262bfdea254240d9846700da3933baf1
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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