3-Nitrophenol → Nitro-3-[2-(4-cyanophenyl)ethoxy]benzene

HRID 325027Notes

Reaction equation

HRID 325027 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[N+:32]([C:35]1[CH:36]=[C:37]([OH:41])[CH:38]=[CH:39][CH:40]=1)([O-:34])=[O:33].[C:42]([C:44]1[CH:49]=[CH:48][C:47]([CH2:50][CH2:51]O)=[CH:46][CH:45]=1)#[N:43]>C1COCC1.O>[N+:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH2:51][CH2:50][C:47]2[CH:48]=[CH:49][C:44]([C:42]#[N:43])=[CH:45][CH:46]=2)[CH:36]=1)([O-:34])=[O:33]

Participants

7

Reactant 4

HCID 111373-NitrophenolHCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22033514Nitro-3-[2-(4-cyanophenyl)ethoxy]benzeneYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (11.3 g; 43.1 mmol) and diethylazodicarboxylate (7.5 g; 43 mmol) were dissolved in THF (250 mL) under nitrogen at 0° C. After 5 minutes, 3-nitrophenol (5.00 g; 35.9 mmol) and 2-(4-cyanophenyl)ethanol (6.3 g; 43 mmol) were added. The cooling bath was removed and the mixture stirred for 2 days at room temperature. A new batch was prepared as above and the two were combined before work-up. Water was added and the THF was evaporated. The mixture was extracted with EtOAc, and the organic phase was washed with aqueous 0.2M NaOH and brine, dried (Na2SO4) and the solvent removed in vacuo. Purification by flash chromatography (SiO2; toluene) and recrystallization from CH2Cl2:EtOH afforded 3.07 g (32%) of the sub-title compound.

Workup

  1. customThe cooling bath was removed
  2. customA new batch was prepared as above and the two
  3. customthe THF was evaporated
  4. extractionThe mixture was extracted with EtOAc
  5. washthe organic phase was washed with aqueous 0.2M NaOH and brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed in vacuo
  8. customPurification
  9. customby flash chromatography (SiO2; toluene) and recrystallization from CH2Cl2

Sources & evidence

ORD record
ord-5a2211590a334c419b0a814e788018ae
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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