Water → 4-(4-Bromophenoxy)-2,5-dimethylnitrobenzene

HRID 405003Notes

Reaction equation

HRID 405003 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[C:18]([CH3:26])[CH:17]=1.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[C:18]([CH3:26])[CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 2527931-Chloro-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 685953564-(4-Bromophenoxy)-2,5-dimethylnitrobenzeneYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

37.5 g (216.7 mmol) of 4-bromophenol and 35.4 g (256.2 mmol) of potassium carbonate are suspended in 500 ml of N,N-dimethylformamide and the suspension is stirred at room temperature for 1 h, before 36.6 g (197.0 mmol) of 4-chloro-2,5-dimethylnitrobenzene are added. The mixture is subsequently stirred at 150° C. for 14 h, water is added, and repeated extraction is carried out with ethyl acetate. The extracts are dried over Na2SO4 and filtered and the solvent is removed under reduced pressure. This is followed by purification by column chromatography (48.0 g, purity 91.0%, yield 68.8%, log P (pH 2.3)=4.86).

Workup

  1. additionare added
  2. extractionextraction
  3. dry with materialThe extracts are dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThis is followed by purification by column chromatography (48.0 g, purity 91.0%, yield 68.8%, log P (pH 2.3)=4.86)

Sources & evidence

ORD record
ord-57c2386e089940c09c2e46307af27afd
Source dataset
uspto-grants-2014_06
Patent number
US08748662B2

Reaction notes

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