Reaction #65100

Reaction equation

4-methoxy-3-fluoro-benzene boronic acid

4-bromo-4'-cyanobiphenyl

sodium carbonate

benzene

→

4-methoxy-3-fluoro-4"-cyano-p-terphenyl

Yield 88.6%

Solvents

ethanol

Conditions

Workup

1. 1
   Othera solution which was prepared
2. 2
   workup.ADDITIONwas slowly added dropwise
3. 3
   Temperatureto reflux for 8 hours
4. 4
   Temperaturethe solution was cooled
5. 5
   Otherthe crystals thus precipitated
6. 6
   Otherwere separated by filtration
7. 7
   Washwashed with water and methanol in turn
8. 8
   Otherdried

Procedure

To a mixture of 2.4 g of 4-bromo-4'-cyanobiphenyl, 0.37 g of tetrakis(triphenylphosphine)palladium(0), 15.2 ml of a 2N aqueous sodium carbonate solution, and 19.4 ml of benzene, a solution which was prepared by dissolving 1.9 g of 4-methoxy-3-fluoro-benzene boronic acid synthesized in [1] above in 14.4 ml of ethanol was slowly added dropwise with stirring, and the solution was subjected to reflux for 8 hours. After the reflux was finished, the solution was cooled, and the crystals thus precipitated were separated by filtration and washed with water and methanol in turn, and dried to obtain 2.5 g of 4-methoxy-3-fluoro-4"-cyano-p-terphenyl.

Source