p-Fluoronitrobenzene → 1-[2,4-Bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]ethanone

HRID 880358

Reaction equation

HRID 880358 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[C:4]([O:12][CH2:13][O:14][CH3:15])[C:3]=1[C:16](=[O:18])[CH3:17].C([O-])([O-])=O.[K+].[K+].[N+:25]([C:28]1[CH:33]=[CH:32][C:31](F)=[CH:30][CH:29]=1)([O-:27])=[O:26]>CS(C)=O.O.C(OCC)(=O)C>[CH3:15][O:14][CH2:13][O:12][C:4]1[CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=[C:2]([O:1][C:31]2[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=2)[C:3]=1[C:16](=[O:18])[CH3:17]

Participants

7

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 108796971-[2-Hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone

Product 1

HCID 667593101-[2,4-Bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]ethanoneYield 52%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone (78 g, 298 mmol) and K2CO3 (45.3 g, 328 mmol) in DMSO (500 mL) and water (40 ml) was added 4-nitro-1-fluorobenzene (46.3 g, 328 mmol, 1.1 eq). After stirring for 15 min. at room temperature, the resulting suspension was heated for 6 hours at 55° C. After cooling, the dark solution was diluted with ethyl acetate (2000 mL) and thoroughly washed with 10% citric acid solution, then with brine and dried over Na2SO4. The solvent was removed and the residue was columned over silica gel eluting with cyclohexane/ethyl acetate 3/1, to provide the title compound (56 g, 52% yield).

Workup

  1. temperaturethe resulting suspension was heated for 6 hours at 55° C
  2. temperatureAfter cooling
  3. washthoroughly washed with 10% citric acid solution
  4. dry with materialwith brine and dried over Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-e370b93d25df41e0848e26659099a52e
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Linked notes

Loading…