Sodium Bicarbonate → HCID 13225968, Verbindung

HRID 1640329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640329
[Br:1][C:2]1[O:3][C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]=1[CH2:7]Br.C([O-])(O)=[O:14].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[O:3][C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]=1[CH2:7][OH:14]

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 123374992-Bromo-3-(bromomethyl)-1-benzofuran

Produkt 1

HCID 13225968HCID 13225968, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-bromo-3-bromomethyl benzofuran prepared from Step A (7.67 g, 26.45 mmol) was immediately dissolved in dioxane (30 mL), followed by a solution of NaHCO3 (2.67 g, 1.2 eq.) in water (30 mL). The mixture was refluxed for 1 h with vigorous stirring, cooled to room temperature, diluted with water (150 mL) and extracted with dichloromethane (5×100 mL). The extract was washed with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The resulting orange oil was dissolved in chloroform (12 mL) and left to stand at −20° C. The resulting yellow prisms were filtered at −40° C., washed with chloroform, and filtered cold. Yield: 3.72 g (62%). MS (m/e): 228, 226 (M+), 211, 209, 183, 181, 171, 169, 147, 118, 102, 91. 1H-NMR (acetone-D6): 4.29 (t, 1H, J=6 Hz) 4.73 (d, 2H, J=6 Hz) 7.32 (m, 2H) 7.51 (d, 1H, J=8 Hz) 7.78 (dd, 1H, J=8 Hz, 2 Hz). 13C-NMR (acetone-D6): 54.74, 110.64, 119.96, 123.28, 124.57, 126.51, 128.12, 155.37.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 h with vigorous stirring
  2. extractionextracted with dichloromethane (5×100 mL)
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe resulting orange oil was dissolved in chloroform (12 mL)
  7. waitleft
  8. customto stand at −20° C
  9. filtrationThe resulting yellow prisms were filtered at −40° C.
  10. washwashed with chloroform
  11. filtrationfiltered cold

Quellen und Nachweise

ORD-Eintrag
ord-4ea146ff678d4503b81dfc10b9d235df
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114382B2

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