4'-bromo-[1,1'-Biphenyl]-4-carbonitrile → 4'-Furan-3-yl-biphenyl-4-carbonitrile
Reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:3][CH:2]=1.BrC1C=CC(C2C=CC([C:31]#[N:32])=CC=2)=CC=1>CO>[O:9]1[CH:10]=[CH:11][C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:12]3[CH:17]=[CH:16][C:15]([C:31]#[N:32])=[CH:14][CH:13]=3)=[CH:2][CH:3]=2)=[CH:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
As described in Example 1(a) for the preparation of 3-biphenyl-4-yl-furan, crude 4′-bromo-biphenyl-4-carbonitrile (200 mg, 0.775 mmol) and 3-fuiranboronic acid (see Thompson, W. J.; Gaudino, G. J. Org. Chem. 1984, 49, 5237-5243; 105 mg, 0.937 mmol) in MeOH (2 mL) were coupled to give a yellow solid, which was purified via preparative TLC. Elution with EtOAc:benzene (1:99) provided 100 mg (53%) of 4′-furan-3-yl-biphenyl-4-carbonitrile as a grey powder, mp 199-203° C.