Methyl iodide → 1-Ethyl-2-methoxy-4-nitrobenzene

HRID 1916368Notes

Reaction equation

HRID 1916368 reaction equation
[CH2:1](C1C=CC=CC=1N)C.[CH2:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[OH:21])[CH3:11].C([O-])([O-])=O.[K+].[K+].CI>CC(C)=O.O>[CH2:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH3:1])[CH3:11]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 113572-EthylanilineHCID 11430Potassium CarbonateHCID 189800772-Ethyl-5-nitrophenol2×

Product 1

HCID 576576411-Ethyl-2-methoxy-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Following published procedures 2-ethyl aniline was nitrated (Bergman, J.; Sand, P. Tetrahedron 1990, 46, 1085) and then converted to 2-ethyl-5-nitrophenol (PCT WO 1995/15954). A mixture of 2-ethyl-5-nitrophenol (0.320 g, 1.92 mmol), K2CO3 (0.200 g, 1.44 mmol) and MeI (0.300 g, 2.11 mmol) in acetone (4.0 mL) was heated at 70° C. for 15 h. The solution was cooled to rt, diluted with H2O, concentrated and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the title compound (0.347 g) as an orange oil which was used in the next step without further purification. HPLC (Method #1): 3.46 min retention time, (75%); LCMS (ES): m/z 182 [M+H]+.

Workup

  1. temperatureThe solution was cooled to rt
  2. concentrationconcentrated
  3. extractionextracted with CH2Cl2 (3×30 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b13795afd3654260a7102d7f7fabf91f
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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