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Potassium Carbonate → 3-(2-Nitrophenoxy)benzonitrile

HRID 12175
Notes
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Reaction equation

HRID 12175 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])([O-:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 91948883-(2-Nitrophenoxy)benzonitrileYield 99.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-fluoro nitrobenzene (1.41 g, 10 mmol, 1.0 equiv) and 3-hydroxybenzonitrile (1.19 g, 1.0 equiv) in 10 mL of DMF was added K2CO3 (2.76 g, 2 equiv). After stirring at 60° C. for 3 h, the mixture was diluted with EtOAc and washed with H2O. The organic layer was dried over MgSO4, filtered and evaporated to give 3-(2-nitrophenoxy)benzonitrile (2.38 g, 99%). MS found for C13H9N2O3 (M+H)+: 241.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0cd93d207e004979a92ba2c0b525333b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07727981B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes