Ethanol → 2-Ethoxy-4-fluoronitrobenzene

HRID 1282083Notes

Reaction equation

HRID 1282083 reaction equation
[CH2:1]([OH:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:23][C:24]1[CH:25]=[CH:26][C:27]([N+:31]([O-:33])=[O:32])=[C:28](O)[CH:29]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:26]1[CH:25]=[C:24]([F:23])[CH:29]=[CH:28][C:27]=1[N+:31]([O-:33])=[O:32])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 129181532-Ethoxy-4-fluoronitrobenzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethanol (4.2 ml) in tetrahydrofuran (65 ml) was added a solution of triphenylphosphine (13 g) and 5-fluoro-2-nitrophenol (10 g) in tetrahydrofuran (65 ml). To this solution was added diethyl azodicarboxylate (10 ml) under ice-cooling and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure and diisopropyl ether was added. The precipitated crystals were collected by filtration and concentrated under reduced pressure. The concentrate was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give a yellow oil. To this oil was added ethyl acetate, washed with an aqueous sodium hydroxide solution, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (9.6 g) as a yellow oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure and diisopropyl ether
  3. additionwas added
  4. filtrationThe precipitated crystals were collected by filtration
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow oil
  7. washwashed with an aqueous sodium hydroxide solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9101ff535b44bc8a08ac03a994a6ea4
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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