Benzonitrile, 4-bromo- → [1,1':4',1''-Terphenyl]-4,4''-dicarbonitrile

HRID 422121

Reaction equation

HRID 422121 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:10]2[CH:15]=[CH:14][C:13]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)=[CH:12][CH:11]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

3

Reactant 2

HCID 12162Benzonitrile, 4-bromo-HCID 2304781,4-Benzenediboronic acid

Product 1

HCID 66675539[1,1':4',1''-Terphenyl]-4,4''-dicarbonitrileYield 73%

Procedure

The same procedure described for 1 was used by employing 4-bromobenzonitrile (2 equiv.) and 1,4-phenylenebisboronic acid (1 equiv.) to furnish 17 as a white solid in 73% yield; mp 299-300° C. 1H NMR (DMSO-d6): δ 7.89 (dd, J=8.1, 2.1 Hz, 4H), 7.94-7.96 (m, 8H). MS (ESI) m/e (rel. int.): 280 (M+, 100). Anal. Calc. for C20H12N2: C %, 85.69; H %, 4.31. Found C %, 85.41; H %, 4.52.

Sources & evidence

ORD record
ord-92573a5688224ef398bf053d388ed8df
Source dataset
uspto-grants-2012_01
Patent number
US08101636B2

Linked notes

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