Réaction #84783

Équation de réaction

3,5-dimethoxy-4-bromo-iodobenzene

2-furylboronic acid

Na2CO3

THF

→

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

Rendement 91.2%

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   Autre2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized
2. 2
   AutreThe 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
   TempératureAfter cooling to room temperature
6. 6
   Filtrationthe mixture was filtered through Celite
7. 7
   Lavagerinsed with THF and EtOAc
8. 8
   AutreThe filtrate layers were separated
9. 9
   Lavagethe organic layer was washed with brine
10. 10
    Séchagedried over Na2SO4
11. 11
    Concentrationconcentrated
12. 12
    AutrePurification by column chromatography (0-25% Et2O-hexanes)

Mode opératoire

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).

Source