Phenylboronic Acid → 5-Bromo-1-chloro-3-methyl-2-phenoxybenzene

HRID 449108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449108
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([Cl:10])[CH:3]=1

Komponenten

4

Edukt 2

HCID 66827Phenylboronic AcidHCID 820314-Bromo-6-chloro-o-cresol

Produkt 1

HCID 669155775-Bromo-1-chloro-3-methyl-2-phenoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Into a 100 mL round bottom flask was added 4-bromo-2-chloro-6-methylphenol (1.00 g, 4.52 mmol), benzeneboronic acid (1.10 g, 9.04 mmol), cupric acetate (1.4 g, 7.70 mmol) and DCM (50 mL). TEA (4.0 mL, 29.0 mmol) was then added followed by 4 A° molecular sieves and the reaction mixture was stirred at rt for 48 h. Reaction mixture was then filtered through celite. The filtrate was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 5% EtOAc in hexane.

Aufarbeitung

  1. customReaction mixture
  2. filtrationwas then filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a residue which
  5. customwas purified by silica gel chromatography
  6. washeluting with 5% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-115ac5cd92ce4f1eb6dc9240532118fd
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481733B2

Notizen zur Reaktion

Wird geladen…