Reaktion #84783

Reaktionsgleichung

3,5-dimethoxy-4-bromo-iodobenzene

2-furylboronic acid

Na2CO3

THF

→

2-(4-bromo-3,5-dimethoxyphenyl)furan

Ausbeute 91.2%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized
2. 2
   SonstigeThe mixture was degassed
3. 3
   workup.WAITby alternately putting under house vacuum and argon three times for several minutes
4. 4
   workup.ADDITION10% Pd/C (1.36 g) was added
5. 5
   TemperaturAfter cooling to room temperature
6. 6
   Filtrationthe mixture was filtered through Celite
7. 7
   Waschenrinsed with THF and EtOAc
8. 8
   SonstigeThe filtrate layers were separated
9. 9
   Waschenthe organic layer was washed with brine
10. 10
    Trocknendried over Na2SO4
11. 11
    Einengenconcentrated
12. 12
    SonstigePurification by column chromatography (0-25% Et2O-hexanes)

Vorschrift

2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized according to the procedure reported in WO 2008/040669 as follows. To a round bottom flask containing 3,5-dimethoxy-4-bromo-iodobenzene (7.9 g, 85% purity, 19.6 mmol), 2-furylboronic acid (3.4 g, 30.4 mmol), triphenylphosphine (0.358 g, 1.37 mmol), tetrabutylammonium bromide (7.94 g, 14.6 mmol) and Na2CO3 (4.9 g, 46.2 mmol) was added THF (87 mL) and H2O (87 mL). The mixture was degassed by alternately putting under house vacuum and argon three times for several minutes each. 10% Pd/C (1.36 g) was added and the mixture was heated at 60° C. for 17 hrs under argon. After cooling to room temperature, the mixture was filtered through Celite and rinsed with THF and EtOAc. The filtrate layers were separated and the organic layer was washed with brine, dried over Na2SO4 and concentrated. Purification by column chromatography (0-25% Et2O-hexanes) gave 2-(4-bromo-3,5-dimethoxyphenyl)furan as a white solid (5.06 g, 91% yield). Product TLC Rf 0.35 (15% EtOAc-hexanes TLC eluent).

Quelle