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Ammonium Chloride → Bnc-105

HRID 218833
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 218833
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23](OC)[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[CH3:31]B(O)O.[C:35](=[O:38])(O)[O-].[Na+].[Cl-].[NH4+]>O1CCOCC1.O.ClCCl>[CH3:31][C:2]1[O:3][C:4]2[C:24]([OH:25])=[C:23]([O:38][CH3:35])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 139377Methylboronic AcidHCID 516892Sodium BicarbonateHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Produkt 1

HCID 24786555Bnc-105

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran (20 mg, 0.042 mmol), methyl-boronic acid (40 mg, 0.67 mmol), in 1,4-dioxane (2 mL) at 90° C. was added tetiakis-triphenylphosphine palladium (11 mg, 0.01 mmol) followed by the addition of a solution of sodium bicarbonate (40 mg, 0.48 mmol) in distilled water (0.5 mL). The reaction mixture turned red after 5 minutes. After 2 hours (tlc) the reaction mixture was brought to room temperature and was added saturated ammonium chloride (2 mL) and diluted with dichloromethane (20 mL). The organic layer was separated and washed with water, dried over magnesium sulfate and the solvent was removed by distillation under vacuum. The residue was purified by PTLC (eluent=Dichloromethane/Methanol, 1:1) to give the title compound (actate cleaved during reaction) as a fluffy white solid; (3 mg, 19%).

Aufarbeitung

  1. waitAfter 2 hours (tlc) the reaction mixture was brought to room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed by distillation under vacuum
  6. customThe residue was purified by PTLC (eluent=Dichloromethane/Methanol, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-99aca2e331dd43f2b9cae83d82d5b0fd
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198466B2

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