p-Fluoronitrobenzene → HCID 22762773, compound

HRID 1112772Notes

Reaction equation

HRID 1112772 reaction equation
[OH:1][C:2]([CH3:18])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[H-].[Na+].[H][H].F[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>[O-2].[O-2].[Mn+4].C1C=CC=CC=1.CN(C)C=O>[N+:30]([C:27]1[CH:28]=[CH:29][C:24]([O:1][C:2]([CH3:18])([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:25][CH:26]=1)([O-:32])=[O:31]

Participants

8

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 22762825HCID 22762825, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22762773HCID 22762773, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

1-[2-Hydroxy-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole (2.60 g.) in 15 ml. of anhydrous dimethylformamide and 7.5 ml. of benzene is treated with 1.12 g. of a 50% dispersion of sodium hydride in mineral oil at room temperature under nitrogen. The mixture is stirred until the evolution of hydrogen ceases and then cooled in ice and treated with 900 mg. of manganese dioxide followed by 2.55 g. of 1-fluoro-4-nitrobenzene. After stirring for 3-4 hours at room temperature, the mixture is poured into 150 ml. of water, extracted with ether and the combined extracts washed with water, dried (MgSO4) and evaporated to yield 1-[2-(4-nitrophenoxy)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole which may be purified, if necessary, by chromatography on silica gel eluting with 5-10% methanol in methylene chloride.

Workup

  1. customat room temperature
  2. temperaturecooled in ice
  3. additiontreated with 900 mg
  4. additionthe mixture is poured into 150 ml
  5. extractionof water, extracted with ether
  6. washthe combined extracts washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-549b6c59df9d46439704feba5a9465c1
Source dataset
uspto-grants-1978_10
Patent number
US04123542

Reaction notes

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