반응 #599786

반응 방정식

3,5-dimethoxy-4-bromo-iodobenzene

2-furylboronic acid

Na2CO3

THF

→

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

수율 91.2%

용매

H2O

반응 조건

후처리

1. 1
   기타2-(4-Bromo-3,5-dimethoxyphenyl)furan was synthesized
2. 2
   기타The 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
   온도After cooling to room temperature
6. 6
   여과the mixture was filtered through Celite
7. 7
   세척rinsed with THF and EtOAc
8. 8
   기타The filtrate layers were separated
9. 9
   세척the organic layer was washed with brine
10. 10
    건조dried over Na2SO4
11. 11
    농축concentrated
12. 12
    기타Purification by column chromatography (0-25% Et2O-hexanes)

실험 절차

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).

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