반응 #1885002

반응 방정식

4-bromo-3-fluorophenol

3,4,5-trifluorophenyl-boric acid

sodium carbonate

dimethoxyethane water

→

3-fluoro-4-(3,4,5-trifluorophenyl)phenol

수율 81.5%

용매

toluene

반응 조건

후처리

1. 1
   온도Next, the reaction solution was cooled to room temperature
2. 2
   세척washed with 1N hydrochloric acid and water
3. 3
   건조Afterwards, the solution was dried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under reduced pressure
5. 5
   기타to remove the solvent
6. 6
   기타Subsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent
7. 7
   기타dried under reduced pressure
8. 8
   기타The obtained residue was recrystallized in heptane

실험 절차

At first, 75.0 g of 4-bromo-3-fluorophenol (S3-1), 82.9 g 3,4,5-trifluorophenyl-boric acid (S3-2), 13.6 g of tetrakis(triphenylphosphine)palladium, 108.5 g of sodium carbonate and 1100 ml of a mixed solvent of dimethoxyethane/water=2/1 (volume ratio) were added into a reactor under nitrogen atmosphere, and the mixture was heated to 80° C. and stirred for 4 hr. Next, the reaction solution was cooled to room temperature, added with toluene and then washed with 1N hydrochloric acid and water. Afterwards, the solution was dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. Subsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent and then dried under reduced pressure. The obtained residue was recrystallized in heptane to obtain 77.5 g of 3-fluoro-4-(3,4,5-trifluorophenyl)phenol (S3-3). The yield of (S3-3) from (S3-1) was 81.5%.

출처