Dichloromethane → 5-Bromo-1,3-dimethoxy-2-phenoxybenzene

HRID 449089

Reaktionsgleichung

Reaktionsgleichung von HRID 449089
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)Cl>>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([O:8][CH3:9])[CH:7]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 148458764-Bromo-2,6-dimethoxyphenol

Produkt 1

HCID 690021665-Bromo-1,3-dimethoxy-2-phenoxybenzene

Versuchsvorschrift

4-bromo-2,6-dimethoxyphenol (500 mg, 0.002 mol), phenylboronic acid (0.65 g, 0.0054 mol), TEA (1.8 mL, 0.013 mol), cupric acetate (0.62 g, 0.0034 mol) and DCM (30 mL, 0.4 mol) were added to a 100 mL oven dried flask and the reaction 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. 1H NMR (400 MHz, CDCl3): δ=3.77 (s, 6H), 6.82 (s, 2H), 6.86 (d, J=7.83 Hz, 2H), 6.96-7.04 (m, 1H), 7.22-7.27 (m, 2H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-db395168de0d43f5bfbef93e02fa65b2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481733B2

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