반응 #42470

반응 방정식

Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

BBr3

→

title compound

수율 88.5%

Methyl 3-bromo-5-(butylamino)-4-hydroxybenzoate

수율 88.5%

용매

methylene chloride

반응 조건

후처리

1. 1
   농축The mixture was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in methylene chloride
3. 3
   workup.ADDITIONsaturated sodium bicarbonate was added
4. 4
   workup.ADDITIONmethanol was added dropwise
5. 5
   workup.STIRRINGAfter stirring for 30 min
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for 1 h
7. 7
   기타The solvent was removed
8. 8
   workup.DISSOLUTIONthe residue dissolved in methylene chloride
9. 9
   세척washed with water, saturated sodium bicarbonate (15 mL), and brine
10. 10
    건조dried (magnesium sulfate)
11. 11
    여과filtered
12. 12
    농축concentrated under reduced pressure
13. 13
    기타Purification by flash column chromatography (silica, 1:20, ethyl acetate/hexanes)

실험 절차

To a −78° C. solution of the Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate (520 mg) in methylene chloride (10 mL) was added BBr3 (8 ml of 1.0 M solution in methylene chloride) dropwise and the reaction mixture was stirred for 18 h. The mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride and saturated sodium bicarbonate was added. The mixture was cooled to 0° C. and methanol was added dropwise. After stirring for 30 min, the mixture was stirred at room temperature for 1 h. The solvent was removed, and the residue dissolved in methylene chloride, washed with water, saturated sodium bicarbonate (15 mL), and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:20, ethyl acetate/hexanes) provided 440 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.88, 3.18, 1.65, 1.46, 0.97.

출처