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

HRID 1106732
Notes
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Reaction equation

HRID 1106732 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 8857
Ethyl Acetate
Solvent

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-01dc3a32a540408ca9b6d8c1498c25ce
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06057349

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes