Benzonitrile, 4-bromo- → 4'-bromo-[1,1'-Biphenyl]-4-carbonitrile

HRID 566765Notes

Reaction equation

HRID 566765 reaction equation
C1(C2C=CC=CC=2)C=CC(C2C=COC=2)=CC=1.Br[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.[Br:27][C:28]1[CH:33]=[CH:32][C:31](OB(O)O)=[CH:30][CH:29]=1>CCO>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 3155134-Bromophenyl-boric acidHCID 183802933-(Biphenyl-4-yl)furan

Product 1

HCID 13944624'-bromo-[1,1'-Biphenyl]-4-carbonitrileYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As described in Example 1(a) for the preparation of 3-biphenyl-4-yl-furan, 4-bromobenzonitrile (9.42 g, 51.8 mmol) and 4-bromophenylboric acid (5.20 g, 25.9 mmol) were coupled in EtOH to afford 4.50 g (67%) of 4′-bromo-biphenyl-4-carbonitrile as a grey powder, mp 147-8° C. (lit 153-5° C.; McNamara, J.; Gleason, W. B. J. Org. Chem. 1976, 41, 1071). The material had an NMR spectrum that matched literature (see Amatore, C.; Juland, A.; Negri, S. J. Organomet. Chem. 1990, 390, 389-398) and was typically used without further purification.

Sources & evidence

ORD record
ord-eb60e8168edd4962887bf843b79894a2
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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