反応 #1885002

反応方程式

4-bromo-3-fluorophenol

3,4,5-trifluorophenyl-boric acid

sodium carbonate

dimethoxyethane water

→

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

収率 81.5%

溶媒

toluene

反応条件

後処理

1. 1
   温度Next, the reaction solution was cooled to room temperature
2. 2
   洗浄washed with 1N hydrochloric acid and water
3. 3
   乾燥Afterwards, the solution was dried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under reduced pressure
5. 5
   その他to remove the solvent
6. 6
   その他Subsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent
7. 7
   その他dried under reduced pressure
8. 8
   その他The obtained residue was recrystallized in heptane

実験手順

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%.

出典