Dimethylformamide → HCID 86694551, compound

HRID 714574Notes

Reaction equation

HRID 714574 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 119062-Chlorobenzyl chlorideHCID 12074Nitrofungin

Product 1

HCID 86694551HCID 86694551, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a reaction flask were added 2-chloro-4-nitrophenol (5.205 g, 30 mmol), 2-chlorobenzyl chloride (5.313 g, 33 mmol), potassium carbonate (4.554 g, 33 mmol) and DMF (40 ml). The reaction mixture was heated to the temperature of 100° C. After the reaction finished, the reaction solution was poured into water (400 ml). The mixture was extracted with ethyl acetate (300 ml). The ethyl acetate layer was washed with saturated saline solution (200 ml) once and dried over anhydrous magnesium sulfate. The organic layer was filtered and the solvent was rotary-evaporated to dryness. The resultant substance was recrystallized with ethyl acetate to give 1-(2-chlorobenzyloxy)-2-chloro-4-nitrobenzene (8.567 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (300 ml)
  2. washThe ethyl acetate layer was washed with saturated saline solution (200 ml) once
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe organic layer was filtered
  5. customthe solvent was rotary-evaporated to dryness
  6. customThe resultant substance was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-64ba91379cb144c7b39edfacc170d100
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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