4-Chlorobenzonitrile → 4-(2-methylphenyl)benzonitrile

HRID 412831Notes

Reaction equation

HRID 412831 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[F-].[K+]>C1COCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:10])=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 13928684-(2-methylphenyl)benzonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzonitrile (55 mg, 0.40 mmol) reacted with 2-methylphenylboronic acid (82 mg, 0.60 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (70 mg, 1.21 mmol) in THF at 45° C. to give the title compound (72 mg, 94%) as a white solid: 1H-NMR (300 MHz, CDCl3): δ 7.73 (d, 2H, J=8.1 Hz), 7.46 (d, 2H, J=8.4 Hz), 7.27-7.34 (m, 3H), 7.21, (d, 1H, J=6.9 Hz), 2.80 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.76, 139.97, 135.00, 131.94, 130.64, 129.97, 129.39, 128.26, 126.07, 118.93, 110.70, 20.28. GC/MS (EI): m/z 193 (M+), 165.

Workup

  1. customat 45° C.

Sources & evidence

ORD record
ord-ed022b8edf5f4e128b55be971eb02495
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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