Hydrochloric Acid → 5-Bromo-6-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)nicotinic acid

HRID 598227Notes

Reaction equation

HRID 598227 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:7][C:6]=1[C:18]([F:21])([F:20])[F:19])C.O.[OH-].[Li+].Cl>O1CCCC1.O>[Br:11][C:9]1[C:8]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])=[N:7][C:6]([C:18]([F:21])([F:19])[F:20])=[C:5]([CH:10]=1)[C:4]([OH:22])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 866347975-Bromo-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 863463205-Bromo-6-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)nicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinic acid ethyl ester (4.0 g, 10 mmol) was dissolved in a mixture of tetrahydrofuran (70 mL) and water (25 mL). Lithiumhydroxid monohydrate (1.26 g, 30 mmol) was added and the mixture was stirred and heated at reflux-temperature for 3 h. After cooling to room temperature the mixture was acidified with hydrochloric acid (1N) to pH 4. The product precipitated and was after filtration dried and isolated as a white solid (quant.); MS (ISP) 365.8, 367.8 (M−H).

Workup

  1. temperatureheated
  2. temperatureat reflux-temperature for 3 h
  3. customThe product precipitated
  4. filtrationafter filtration
  5. customdried
  6. customisolated as a white solid (quant.)

Sources & evidence

ORD record
ord-b3992845466d43e79f9e4c720d71188f
Source dataset
uspto-grants-2011_03
Patent number
US07897621B2

Reaction notes

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