Hydrochloric Acid → (5-Methoxy-2-nitrophenyl)acetonitrile

HRID 469287

Reaction equation

HRID 469287 reaction equation
CC(C)([O-])C.[K+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].ClC1C=CC(O[CH2:24][C:25]#[N:26])=CC=1.Cl>CN(C=O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[C:11]([CH2:24][C:25]#[N:26])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74854-NitroanisoleHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 10867168(5-Methoxy-2-nitrophenyl)acetonitrileYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

24.0 g (214 mmol) potassium-tert-butoxide in 100 mL DMF were slowly added dropwise to a solution of 13.17 g (86.0 mmol) 4-nitroanisole and 18.0 g (107 mmol) 4-chlorophenoxyacetonitrile in 50 mL DMF. The reaction mixture was stirred for 30 min at −10° C. and then poured into 300 g of a 1:1 mixture of conc. HCl and ice. After extraction with EtOAc the organic phase was washed with water, dried and concentrated to dryness by rotary evaporation in vacuo with gentle heating. The residue was treated with a 1:1 mixture of PE/EtOAc and the product that crystallised out was suction filtered. After washing with a 1:1 mixture of PE/EtOAc the crystals were dried in the air. 6.5 g of the desired product was obtained.

Workup

  1. extractionAfter extraction with EtOAc the organic phase
  2. washwas washed with water
  3. customdried
  4. concentrationconcentrated to dryness by rotary evaporation in vacuo with gentle heating
  5. additionThe residue was treated with a 1:1 mixture of PE/EtOAc
  6. customthe product that crystallised out
  7. filtrationfiltered
  8. washAfter washing with a 1:1 mixture of PE/EtOAc the crystals
  9. customwere dried in the air

Sources & evidence

ORD record
ord-a5d428de0d334c369a4650bf0acf66ea
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Linked notes

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