Reaction #2348086

Reaction equation

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

3-fluorophenylboronic acid

potassium carbonate

→

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

Yield 81.9%

Solvents

toluene

water

toluene

water

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureunder reflux for 8 hours
3. 3
   workup.ADDITIONmixed
4. 4
   Otherto be separated into two layers of an organic layer
5. 5
   ExtractionExtraction into an organic layer
6. 6
   WashThe extracts were washed with water
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   ConcentrationThe resulting solution was concentrated under reduced pressure
9. 9
   Otherthe residue was purified by means
10. 10
    Otherof fraction-collecting column chromatography
11. 11
    OtherThe 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
    Otherdried

Procedure

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%.

Source