2-Chloroethyl methyl sulfide → 2-Methoxy-4-(2-methylsulfanyl-ethoxy)-1-nitro-benzene

HRID 417326Notes

Reaction equation

HRID 417326 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+].Cl[CH2:20][CH2:21][S:22][CH3:23]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:20][CH2:21][S:22][CH3:23])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 129005323-Methoxy-4-nitrophenol

Product 1

HCID 666255842-Methoxy-4-(2-methylsulfanyl-ethoxy)-1-nitro-benzeneYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Step A To a solution of 3-methoxy-4-nitrophenol (0.5 g, 3 mmol) prepared in Example 132 Step A in anhydrous DMF (13 mL) were added K2CO3 (0.8 g, 5.9 mmol) and 1-Chloro-2-methylsulfanyl-ethane (Aldrich)(0.65 g, 5.9 mmol) sequentially. The reaction mixture was heated at 70° C. for 2 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. The residue was purified by chromatography (0-40% EtOAc in hexanes) to give 2-methoxy-4-(2-methylsulfanyl-ethoxy)-1-nitro-benzene as a white solid (0.25 g, 35%).

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
  7. customThe residue was purified by chromatography (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-dd1893be37c74d52ba2f17ea018ee471
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

Loading…