Benzene, 1-bromo-3-iodo- → 5-(3-Bromophenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-[1,2,4]triazole

HRID 586313Notes

Reaction equation

HRID 586313 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1.C([Li])CCC.I[C:20]1[CH:21]=[C:22]([Br:26])[CH:23]=[CH:24][CH:25]=1>[Cl-].[Zn+2].[Cl-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:26][C:22]1[CH:21]=[C:20]([C:11]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:13])([CH3:12])[CH3:1])[N:8]=[CH:9][N:10]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 11561Benzene, 1-bromo-3-iodo-HCID 148754211-((2-(Trimethylsilyl)Ethoxy)Methyl)-1H-1,2,4-TriazoleHCID 178418339Butyllithium

Product 1

HCID 223295195-(3-Bromophenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-[1,2,4]triazoleYield 31.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

This reaction was carried out as described in Example 40, step a, using 1-(2-trimethylsilanylethoxymethyl)-1H-[1,2,4]triazole (5.34 g, 26.8 mmol), butyllithium (26.8 mmol, 1.6 M in hexanes, 16.8 ml), zinc chloride (3.65 g, 26.8 mmol), 3-iodobromobenzene (3.42 ml, 26.8 mmol) and dichlorobis(triphenylphosphine)palladium(II) (942 mg, 5 mol %) to yield the title compound (2.98 g, 31%): 1H NMR (360 MHz, CDCl3) δ 8.11 (1H, s), 7.94 (1H, s), 7.86 (1H, d, J 7.7 Hz), 7.62 (1H, d, J 7.8 Hz), 7.37 (1H, t, J 7.8 Hz), 5.49 (2H, s), 3.79 (2H, t, J 8.3 Hz), 0.97 (2H, t, J 8.3 Hz), 0.00 (9H, s).

Sources & evidence

ORD record
ord-b5364c73204240918b03ee774c3ee907
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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