Benzonitrile, 4-bromo- → 4'-Formyl-biphenyl-4-carbonitrile

HRID 412804Notes

Reaction equation

HRID 412804 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH:10]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)=[O:11].[F-].[K+]>C1COCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:15]2[CH:16]=[CH:17][C:12]([CH:10]=[O:11])=[CH:13][CH:14]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 522689Potassium FluorideHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27592144'-Formyl-biphenyl-4-carbonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromobenzonitrile (73 mg, 0.40 mmol) reacted with 4-formylphenylboronic acid (90 mg, 0.60 mmol) using 0.5/1.0 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (70 mg, 1.21 mmol) in THF solvent at 40° C. to give the title compound (83 mg, 97%) as a white solid: 1H-NMR (500 MHz, CDCl3): δ 10.10 (s, 1H), 8.01 (d, 2H, J=8.25 Hz), 7.80-7.74 (m, 6H). 13C{1H}-NMR (125 MHz, CDCl3): δ 191.57, 144.90, 144.14, 136.14, 132.78, 130.41,128.03, 127.91, 118.52, 112.17. GC/MS(EI): m/z 207 (M+), 206.

Workup

  1. customat 40° C.

Sources & evidence

ORD record
ord-d287d34348f64f32a62ff4c7ba0eb1ee
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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