反应 #2348086

反应方程式

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

3-fluorophenylboronic acid

potassium carbonate

→

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

收率 81.9%

溶剂

toluene

water

toluene

water

反应条件

后处理

1. 1
   温度heated
2. 2
   温度under reflux for 8 hours
3. 3
   workup.ADDITIONmixed
4. 4
   其他to be separated into two layers of an organic layer
5. 5
   萃取Extraction into an organic layer
6. 6
   洗涤The extracts were washed with water
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   浓缩The resulting solution was concentrated under reduced pressure
9. 9
   其他the residue was purified by means
10. 10
    其他of fraction-collecting column chromatography
11. 11
    其他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
    其他dried

实验过程

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%.

来源