Potassium Carbonate → 2-(4-Methyl-imidazol-1-yl)-5-trifluoromethoxy benzonitrile

HRID 2113447Notes

Reaction equation

HRID 2113447 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)OC1C=CC(N2C(C)=CN=C2)=C(C=1)C#N>>[F:12][C:11]([F:14])([F:13])[O:10][C:7]1[CH:8]=[CH:9][C:2]([N:19]2[CH:20]=[C:16]([CH3:15])[N:17]=[CH:18]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 52210952-Fluoro-5-(trifluoromethoxy)benzonitrileHCID 684064742-(5-Methyl-imidazol-1-yl)-5-trifluoromethoxy-benzonitrileHCID 178418800HCID 178418800, compound

Product 1

HCID 675493282-(4-Methyl-imidazol-1-yl)-5-trifluoromethoxy benzonitrile

Procedure

In analogy to example 5a, 2-fluoro-5-trifluoromethoxy-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. Aqueous workup afforded a 3:1 mixture of the title compound and its regioisomer [5-trifluoromethoxy-2-(5-methyl-imidazol-1-yl)-benzonitrile] as a light brown viscous oil (yield: 100%). 1H-NMR (300 MHz, DMSO): δ=2.19 (s, 3H), 7.37 (s, 1H), 7.75-7.90 (m, 2H), 8.02 (s, 1H), 8.27 (d, J=2.7 Hz, 1H).

Workup

  1. customAqueous workup afforded

Sources & evidence

ORD record
ord-989279651b2d432e9ba842521140fc02
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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