p-Fluoronitrobenzene → HCID 66759784, compound

HRID 880356Notes

Reaction equation

HRID 880356 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[C:4]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:3]=1[C:22](=[O:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].F[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1>CS(C)=O>[CH3:21][O:20][CH2:19][CH2:18][O:17][CH2:16][O:15][C:4]1[CH:5]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=[C:2]([O:1][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)[C:3]=1[C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 12044953HCID 12044953, compound

Product 1

HCID 66759784HCID 66759784, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 1-{2-hydroxy-4,6-bis[(2-methoxyethoxy)methoxy]phenyl}ethanone (2.1 g, 6 mmol), potassium carbonate (0.85 g, 6 mmol) and 1-fluoro-4-nitrobenzene (0.86 g, 6.1 mmol) in DMSO (5 mL) was heated at 80° C. overnight. After dilution with ethyl acetate, the suspension was washed with brine and dried. After removal of the solvent, the residue was chromatographed on silica gel eluting with hexane/ethyl acetate 6/4 to afford the title compound (1.6 g, 54% yield).

Workup

  1. washAfter dilution with ethyl acetate, the suspension was washed with brine
  2. customdried
  3. customAfter removal of the solvent
  4. customthe residue was chromatographed on silica gel eluting with hexane/ethyl acetate 6/4

Sources & evidence

ORD record
ord-83fe54b5390d477ba116a7740bf84b2f
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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