Sodium Carbonate → 2-(4-bromophenyl)benzonitrile

HRID 1990059Notes

Reaction equation

HRID 1990059 reaction equation
I[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 27593582-Iodobenzonitrile

Product 1

HCID 13943922-(4-bromophenyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Combine 2-iodobenzonitrile (9.0 g, 38.5 mmol), 4-bromophenylboronic acid (10.4 g, 51.8 mmol), 2M aqueous sodium carbonate (20 mL) and tetrakis(triphenylphosphine)-palladium(0) (4.5 g, 3.9 mmol) in 300 mL of dioxane and heat to 80° C. under nitrogen with stirring. After 3 hours cool to room temperature and dilute with 900 mL of ethyl acetate. Wash with water (2×50 mL), brine (1×50 mL) and dry over sodium sulfate. Filter and evaporate to a yellow solid. Chromatograph on silica gel two times, eluting with a gradient of 100% toluene to 1/9 ethyl acetate/toluene to give the title compound as a tan solid, 5.42 g (55%). MS (FAB)=257 (M+); HPLC analysis is 95%.

Workup

  1. washWash with water (2×50 mL), brine (1×50 mL)
  2. dry with materialdry over sodium sulfate
  3. filtrationFilter
  4. customevaporate to a yellow solid
  5. washChromatograph on silica gel two times, eluting with a gradient of 100% toluene to 1/9 ethyl acetate/toluene

Sources & evidence

ORD record
ord-51820428b26c4bef9e196e4b1c6172ee
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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