반응 #1964422

반응 방정식

Phosphate

2-(5-bromo-2-methylthiophen-3-yl)-1,3-dioxolane

4-(trifluoromethyl)phenylboronic acid

sodium carbonate

hydrochloric acid

→

title compound

수율 66.1%

2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehyde

수율 66.1%

용매

N,N-dimethylformamide

water

tetrahydrofuran

dichloromethane

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The extract was washed with saturated sodium hydrogen carbonate and saturated brine
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)
8. 8
   기타to give a pale-yellow solid
9. 9
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
10. 10
    기타Tetrahydrofuran was evaporated
11. 11
    기타evaporator
12. 12
    추출the mixture was extracted with ethyl acetate
13. 13
    세척The extract was washed with saturated brine
14. 14
    건조dried over magnesium sulfate
15. 15
    농축concentrated under reduced pressure

실험 절차

To a mixture of 2-(5-bromo-2-methylthiophen-3-yl)-1,3-dioxolane (3.25 g) synthesized in Example 278 (3), 4-(trifluoromethyl)phenylboronic acid (3.70 g), sodium carbonate (2.76 g), water (10 mL) and N,N-dimethylformamide (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II).dichloromethane adduct (1.06 g). The reaction mixture was deaerated and stirred at 80° C. for 4 hr under an argon atmosphere. Phosphate buffer was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give a pale-yellow solid. To a solution of the obtained solid in tetrahydrofuran (25 mL) was added 1N hydrochloric acid (10 mL), and the mixture was stirred at room temperature for 1 hr. Tetrahydrofuran was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (2.33 g, 66%) as a white solid.

출처