Potassium Carbonate → 2-Bromo-1-(3,5-difluoro-2-nitrophenyl)-4-methyl-1H-imidazole

HRID 254323Notes

Reaction equation

HRID 254323 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11].[Br:13][C:14]1[NH:15][CH:16]=[C:17]([CH3:19])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:13][C:14]1[N:15]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=2[N+:10]([O-:12])=[O:11])[CH:16]=[C:17]([CH3:19])[N:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 675671,3,5-Trifluoro-2-nitrobenzeneHCID 178430836HCID 178430836, compound

Product 1

HCID 577324532-Bromo-1-(3,5-difluoro-2-nitrophenyl)-4-methyl-1H-imidazoleYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,3,5-trifluoro-2-nitrobenzene (2.2 mL, 18.6 mmol), 2-bromo-4-methylimidazole (3 g, 18.6 mmol) and K2CO3 (5.66 g, 41 mmol) in 80 mL DMF was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and washed with water. Standard work up procedure followed by column purification using 10% ethyl acetate in dichloromethane as eluent provided 3.18 g (54% yield) of the product as a yellow powder. EIMS 317.9 [M+H]+.

Workup

  1. washwashed with water
  2. customStandard work up procedure followed by column purification

Sources & evidence

ORD record
ord-d7379ae71e1d430ea48eb0bfccc2630d
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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