Potassium Carbonate → Methyl 2-[2-(3-fluoro-4-nitrophenoxymethyl)-5-methylphenoxy]propionate

HRID 257398Notes

Reaction equation

HRID 257398 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl[CH2:13][C:14]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:15]=1[O:16][CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH2:13][C:14]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:15]=1[O:16][CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 15765398Methyl 2-(2-chloromethyl-5-methylphenoxy)propionate

Product 1

HCID 18981042Methyl 2-[2-(3-fluoro-4-nitrophenoxymethyl)-5-methylphenoxy]propionateYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the method of Example 1, Step K, 1.71 g (0.010 mole) of 3-fluoro-4-nitrophenol and 2.85 g (0.011 mole) of methyl 2-(2-chloromethyl-5-methylphenoxy)propionate were reacted in the presence of 1.66 g (0.012 mole) of anhydrous potassium carbonate in 100 mL of N,N-dimethylformamide, yielding 3.55 g of methyl 2-[2-(3-fluoro-4-nitrophenoxymethyl)-5-methylphenoxy]propionate as a yellowish solid, m.p. 92°-94° C. The NMR and IR spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-30f2ab9c8c524cfda81da1cd26a78cf2
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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