4'-bromo-[1,1'-Biphenyl]-4-carbonitrile → 4'-Furan-3-yl-biphenyl-4-carbonitrile

HRID 566766Notes

Reaction equation

HRID 566766 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.O1C=CC(B(O)O)=C1>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]1

Participants

5

Reactant 3

HCID 13944624'-bromo-[1,1'-Biphenyl]-4-carbonitrileHCID 2734358Furan-3-boronic acidHCID 183802933-(Biphenyl-4-yl)furan

Product 1

HCID 183804174'-Furan-3-yl-biphenyl-4-carbonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-furanboronic 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. 1H NMR (CDCl3): δ 7.81 (bs, 1H), 7.72 (d, 4H, J=1.9 Hz), 7.61 (s, 4H), 7.51 (bs, 1H), 6.75 (s, 1H). IR (KBr): 2225, 1604, 1503, 1396, 1162, 1102, 1058 cm−1. Anal. Calculated for C17H11NO•0.3 EtOAc•0.2 C6H6: C, 80.78; H, 5.05; N, 5.01. Found: C, 80.96; H, 4.88; N, 5.00.

Workup

  1. customto give a yellow solid, which
  2. customwas purified via preparative TLC
  3. washElution with EtOAc:benzene (1:99)

Sources & evidence

ORD record
ord-f92e2c583f964dc887b768826b6053e0
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

Loading…