Reacción #84783

Ecuación de reacción

3,5-dimethoxy-4-bromo-iodobenzene

2-furylboronic acid

Na2CO3

THF

→

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

Rendimiento 91.2%

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized
2. 2
   OtroThe 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
   TemperaturaAfter cooling to room temperature
6. 6
   Filtraciónthe mixture was filtered through Celite
7. 7
   Lavadorinsed with THF and EtOAc
8. 8
   OtroThe filtrate layers were separated
9. 9
   Lavadothe organic layer was washed with brine
10. 10
    Secadodried over Na2SO4
11. 11
    Concentraciónconcentrated
12. 12
    OtroPurification by column chromatography (0-25% Et2O-hexanes)

Procedimiento

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).

Fuente