Water → (2-Isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile

HRID 925167Notes

Reaction equation

HRID 925167 reaction equation
N[C:2]1[C:3]([CH:12]([CH3:14])[CH3:13])=[C:4]([OH:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:15]([O-:18])([O-])=O.[K+].[K+].[C:21]([CH2:23]OS(C1C(C)=CC=CC=1)(=O)=O)#[N:22].O>CN(C=O)C>[CH:12]([C:3]1[CH:2]=[C:7]([O:18][CH3:15])[C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=1[O:11][CH2:23][C:21]#[N:22])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67053397HCID 67053397, compoundHCID 88826278HCID 88826278, compound

Product 1

HCID 59598723(2-Isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrileYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-amino-2-isopropyl-5-nitrophenol (9.94 g, 47 mmol), K2CO3 (13.00 g, 94 mmol) and toluenesulfonic acid cyanomethyl ester (10.93 g, 52 mmol) in 500 mL DMF was warmed to 50° C. After 16 h the mixture was cooled, poured into 500 mL H2O and extracted with toluene/ethyl acetate (1:1). The combined organics were washed with H2O, washed with brine, filtered and concentrated in vacuo. The crude solid was recrystallized from EtOH to afford (2-isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile (8.95 g, 76%) as a yellow crystalline solid.

Workup

  1. temperatureAfter 16 h the mixture was cooled
  2. extractionextracted with toluene/ethyl acetate (1:1)
  3. washThe combined organics were washed with H2O
  4. washwashed with brine
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-804ed9a1cd404a0a873ef9a01ef2313e
Source dataset
uspto-grants-2016_03
Patent number
US09284279B2

Reaction notes

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