Potassium Carbonate → 2-Methoxy-4-(3-(methylsulfonyl)propoxy)-1-nitrobenzene

HRID 417339Notes

Reaction equation

HRID 417339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].[CH3:19][S:20]([CH2:23][CH2:24][CH2:25]OS(C)(=O)=O)(=[O:22])=[O:21]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:25][CH2:24][CH2:23][S:20]([CH3:19])(=[O:22])=[O:21])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 102627583-(Methylsulfonyl)propyl methanesulfonateHCID 129005323-Methoxy-4-nitrophenol

Product 1

HCID 666252522-Methoxy-4-(3-(methylsulfonyl)propoxy)-1-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Step B To a solution of 3-methoxy-4-nitrophenol (0.5 g, 3 mmol) prepared in Example 132 Step A in anhydrous DMF (25 mL) were added K2CO3 (0.8 g, 5.9 mmol) and methanesulfonic acid 3-methanesulfonyl-propyl ester (0.7 g, 3.2 mmol) sequentially. The reaction mixture was heated at 70° C. for 4 h. The mixture was cooled to room temperature, and diluted with water. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 2-methoxy-4-(3-(methylsulfonyl)propoxy)-1-nitrobenzene as a off white solid (0.58 g, 68%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-847e28c761324cefae5dca718d8fae0b
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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