Diethyl Ether → 1,2-Dimethyl-3-(4-nitrophenoxy)benzene

HRID 1023557Notes

Reaction equation

HRID 1023557 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=1[OH:25].CCOCC>CN(C)C=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:25][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:18]=2[CH3:17])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9590p-FluoronitrobenzeneHCID 106872,3-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 6181291,2-Dimethyl-3-(4-nitrophenoxy)benzeneYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a microwave vial 1-fluoro-4-nitrobenzene (500 mg, 3.54 mmol) was dissolved in N,N-Dimethylformamide (10 mL) to give a pale yellow solution. Potassium carbonate (1469 mg, 10.63 mmol) and 2,3-dimethylphenol (433 mg, 3.54 mmol) were added. The reaction vessel was sealed and heated in Biotage Initiator at 100° C. for 1 hour. After cooling the reaction was dilued with 25 mL of Et2O. The organic phase was washed with 3 times 25 mL of water, 10 mL of saturated brine, dried over sodium sulphate, filtered and evaporated under vacuum to afford the title compound as a yellow solid (865.1 mg).

Workup

  1. customto give a pale yellow solution
  2. customThe reaction vessel was sealed
  3. temperatureAfter cooling the reaction
  4. washThe organic phase was washed with 3 times 25 mL of water, 10 mL of saturated brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-3490727bbcf94b6ca133d5ad17dfe57a
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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