Hydrochloric Acid → [3-Chloro-5-(2-formyl-4-nitro-phenoxy)-phenyl]acetic acid methyl ester

HRID 656754Notes

Reaction equation

HRID 656754 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([Cl:12])[CH:6]=1.F[C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH:17]=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][C:15]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=2[CH:17]=[O:18])[CH:8]=[C:7]([Cl:12])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27347702-Fluoro-5-nitrobenzaldehydeHCID 58372721Methyl (3-chloro-5-hydroxyphenyl)acetate

Product 1

HCID 58372717[3-Chloro-5-(2-formyl-4-nitro-phenoxy)-phenyl]acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(3-Chloro-5-hydroxy-phenyl)-acetic acid methyl ester (2.9 g, 14.5 mmol), 2-fluoro-5-nitrobenzaldehyde (2.7 g, 15.9 mmol), and potassium carbonate (4.0 g, 28.9 mmol) were combined in 1,4-dioxane (20 mL) and stirred at 100° C. overnight. Once no starting material was seen by analyical LCMS and tlc, the mixture was worked up with EtOAc and 10% aqueous HCl, and the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9de826133baf4d2c867aec7d968ab49c
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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