Dimethylformamide → (4-Benzyloxy-3-nitro-phenoxy)-acetonitrile

HRID 618225Notes

Reaction equation

HRID 618225 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[CH2:26]([O:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18789604(4-Hydroxy-3-nitro-phenoxy)-acetonitrile

Product 1

HCID 18789746(4-Benzyloxy-3-nitro-phenoxy)-acetonitrileYield 80.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A heterogeneous mixture of 6.0 g of (4-hydroxy-3-nitro-phenoxy)-acetonitrile, 50 ml N,N-dimethylformamide, 12.8 g of potassium carbonate, and 5.8 g of benzyl bromide was heated with stirring at 70° C. for 22 hours. The mixture was cooled to room temperature, poured into ethyl acetate, washed with water, washed with 1N sodium hydroxide, again with water, dried (MgSO4), evaporated, and obtained 7.06 g of (4-benzyloxy-3-nitro-phenoxy)-acetonitrile as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water
  4. washwashed with 1N sodium hydroxide, again with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-69c6121f819142b4a8cbf7a90e28cd9f
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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