反応 #2348086

反応方程式

1-iodo-4-(trans-4-pentylcyclohexyl)benzene

3-fluorophenylboronic acid

potassium carbonate

→

3-fluoro-4′-(trans-4-pentylcyclohexyl)biphenyl

収率 81.9%

溶媒

toluene

water

toluene

water

反応条件

後処理

1. 1
   温度heated
2. 2
   温度under reflux for 8 hours
3. 3
   workup.ADDITIONmixed
4. 4
   その他to be separated into two layers of an organic layer
5. 5
   抽出Extraction into an organic layer
6. 6
   洗浄The extracts were washed with water
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   濃縮The resulting solution was concentrated under reduced pressure
9. 9
   その他the residue was purified by means
10. 10
    その他of fraction-collecting column chromatography
11. 11
    その他The residue was further purified by recrystallization from a mixed solvent of ethyl acetate and Solmix A-11 (volume ratio of ethyl acetate Solmix A-11=1:1)
12. 12
    その他dried

実験手順

Into a reaction vessel under an atmosphere of nitrogen, 1-iodo-4-(trans-4-pentylcyclohexyl)benzene (T26; 50.0 g), 3-fluorophenylboronic acid (T27; 21.5 g), potassium carbonate (58.0 g), Pd (Ph3P)2Cl2 (2.95 g), water (200 ml), toluene (200 ml), and Solmix A-11 (200 ml) were put and heated under reflux for 8 hours. After the reaction mixture had been cooled to 25° C., the solution was poured into water (1,000 ml) and toluene (500 ml) and mixed. The mixture was then allowed to stand to be separated into two layers of an organic layer and an aqueous layer. Extraction into an organic layer was carried out and the resulting organic layer was fractionated. The extracts were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by means of fraction-collecting column chromatography using heptane as the eluent and silica gel as the stationary phase powder. The residue was further purified by recrystallization from a mixed solvent of ethyl acetate and Solmix A-11 (volume ratio of ethyl acetate Solmix A-11=1:1) and then dried, whereby 37.3 g of 3-fluoro-4′-(trans-4-pentylcyclohexyl)biphenyl (T28) was obtained. The yield based on the compound (T26) was 82.0%.

出典