Dimethylformamide → 4-Ethoxy-1-fluoro-2-nitrobenzene

HRID 1028222Notes

Reaction equation

HRID 1028222 reaction equation
CN(C=O)C.[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15].[H-].[Na+].[CH2:19](I)[CH3:20]>C(OCC)(=O)C>[CH2:19]([O:13][C:10]1[CH:11]=[CH:12][C:7]([F:6])=[C:8]([N+:14]([O-:16])=[O:15])[CH:9]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 167518614-Fluoro-3-nitrophenol

Product 1

HCID 567772444-Ethoxy-1-fluoro-2-nitrobenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (10 mL) solution of 4-fluoro-3-nitro-phenol (628 mg), sodium hydride (purity: 55% or higher, 209 mg) was added in small portions at room temperature. After 30 minutes, ethyl iodide (0.38 mL) was added thereto at room temperature. After 2 hours, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and saturated brine, then dried over sodium sulfate, and then concentrated. The residue was purified by column chromatography (hexane/ethyl acetate) to obtain the title compound (685 mg, 93%) as a yellow solid.

Workup

  1. customat room temperature
  2. waitAfter 2 hours
  3. washwashed with saturated sodium bicarbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b9e548aa4e894a189a0d38bdd6c2b12a
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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