Diisopropylethylamine → 5-(4-Bromo-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069296Notes

Reaction equation

HRID 2069296 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8](F)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[Br:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:23]2[CH:24]=[C:20]([Br:19])[N:21]=[CH:22]2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl esterHCID 178418934HCID 178418934, compound

Product 1

HCID 693375825-(4-Bromo-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl esterYield 95.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a similar way as in the previous example a solution of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (1 g, 3.73 mmol), 4-bromo-imidazole (0.68 g, 4.5 mmol) and N-ethyl-diisopropyl-amine (2.62 ml, 14.9 mmol) in 10 ml of dioxane is heated to reflux for 16 hours. After a similar workup procedure 1.4 g (3.55 mmol, 95%) of 5-(4-bromo-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester are obtained, m.p. 90° C., ES-MS: m/z 395 [M+H]+.

Workup

  1. temperatureto reflux for 16 hours

Sources & evidence

ORD record
ord-9e07cb99895f45ef8384c669a9dde31d
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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