Methyl 2-[2-(3-fluoro-4-nitrophenoxymethyl)-5-methylphenoxy]propionate → Methyl 2-[2-(4-amino-3-fluorophenoxymethyl)-5-methylphenoxy]propionate

HRID 257399Notes

Reaction equation

HRID 257399 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[N+:24]([O-])=O)[O:5][CH2:6][C:7]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12]>C(O)(=O)C.[Fe]>[NH2:24][C:23]1[CH:22]=[CH:21][C:4]([O:5][CH2:6][C:7]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:8]=2[O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 18981042Methyl 2-[2-(3-fluoro-4-nitrophenoxymethyl)-5-methylphenoxy]propionate

Product 1

HCID 18981068Methyl 2-[2-(4-amino-3-fluorophenoxymethyl)-5-methylphenoxy]propionateYield 61.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

By the method of Example 2, Step A, 3.35 g (0.0091 mole) of methyl 2-[2-(3-fluoro-4-nitrophenoxymethyl)-5-methylphenoxy]propionate was reacted with 2.80 g (0.050 mole) of powdered iron in 100 mL of acetic acid, yielding 1.86 g of methyl 2-[2-(4-amino-3-fluorophenoxymethyl)-5-methylphenoxy]propionate as an amber syrup. The NMR and IR spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-0b2152823d934c8c970b594339abd765
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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