Hydrochloric Acid → 4-(4-Bromo-2,5-dichloro-phenoxy)-6-methyl-nicotinic acid

HRID 1967044Notes

Reaction equation

HRID 1967044 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[C:9]([O:10][C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([Br:18])=[CH:13][C:12]=2[Cl:19])=[CH:8][C:7]([CH3:20])=[N:6][CH:5]=1.O.O.[OH-].[Li+].Cl>O1CCOCC1.ClCCl>[Br:18][C:14]1[C:15]([Cl:17])=[CH:16][C:11]([O:10][C:9]2[C:4]([C:3]([OH:21])=[O:2])=[CH:5][N:6]=[C:7]([CH3:20])[CH:8]=2)=[C:12]([Cl:19])[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 673205494-(4-Bromo-2,5-dichloro-phenoxy)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 673194804-(4-Bromo-2,5-dichloro-phenoxy)-6-methyl-nicotinic acidYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 185 mg (0.473 mmol) 4-(4-bromo-2,5-dichloro-phenoxy)-6-methyl-nicotinic acid methyl ester in 3 mL dioxane was added 3 mL water and 30 mg (0.710 mmol) lithium hydroxide monohydrate. The reaction mixture was stirred for 4 hours at room temperature, poured on 30 mL 1M aqueous hydrochloric acid and 30 mL dichloromethane and the layers were separated. The aqueous layer was extracted with 30 mL dichloromethane and the combined organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum to afford 178 mg (100%) of the title compound as a colorless solid. MS (ESI): m/z=377.912 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 30 mL dichloromethane
  3. washthe combined organic layers were washed with 30 mL brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-47c505cfaaf74e34a84a8434b8e922b1
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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