4-Nitrophenol → 1-(3-Methylbutoxy)-4-nitrobenzene

HRID 2223785Notes

Reaction equation

HRID 2223785 reaction equation
Br[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([O-:9])=[O:8].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:5][CH:4]([CH3:6])[CH2:3][CH2:2][O:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium Carbonate

Product 1

HCID 127211661-(3-Methylbutoxy)-4-nitrobenzeneYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3-methylbutane (7.07 g, 5.60 mL, 46.8 mmol) was added in one portion to a stirred suspension of 4-nitrophenol (5.00 g, 35.9 mmol) and potassium carbonate (5.46 g, 49.5 mmol) in dimethylformamide (50 mL) at room temperature under a nitrogen atmosphere. The resulting mixture was stirred at room temperature for 16 h then the volatiles were evaporated. The residue was partitioned between diethyl ether (50 mL) and water (50 mL) and the phases separated. The aqueous phase was extracted with ether (2×50 mL) then the organic extracts were combined and dried (magnesium sulfate). The solvent was evaporated and the residue chromatographed on silica gel (10% diethyl ether:cyclohexane) to give the title compound as a pale yellow oil (6.63 g, 88%). LC/MS: 3.69 min. 1H NMR (400 MHz; CDCl3): 0.95 (6H), 1.75 (2H), 1.85 (1H), 4.05 (2H), 6.95 (2H), 8.20 (2H).

Workup

  1. customthe volatiles were evaporated
  2. customThe residue was partitioned between diethyl ether (50 mL) and water (50 mL)
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with ether (2×50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customThe solvent was evaporated
  7. customthe residue chromatographed on silica gel (10% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-3543c9d93d6543f4be95084dd362cf4d
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

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