Hydrochloric Acid → 5-Bromo-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid

HRID 1516378Notes

Reaction equation

HRID 1516378 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[OH-].[K+].[F:14][C:15]([F:19])([F:18])[CH2:16][OH:17].Cl>CS(C)=O.O>[Br:1][C:2]1[C:7]([O:17][CH2:16][C:15]([F:19])([F:18])[F:14])=[N:6][CH:5]=[C:4]([CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 14797Potassium HydroxideHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 581925925-Bromo-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

5-Bromo-6-chloro-3-pyridinecarboxylic acid (68.0 g, 0.288 mol, CAN 29241-62-1) was dissolved in DMSO (1000 mL). To this solution was added with stirring potassium hydroxide (48.25 g, 0.86 mol) and after 10 minutes of stirring at room temperature 2,2,2-trifluoroethanol (26.9 mL, 0.374 mol) was added. The mixture was stirred at room temperature for 24 h. Water (1000 mL) and concentrated hydrochloric acid (107 mL, 1280 mmol, 37%) was added and the suspension was stirred vigorously for 4 hours. The precipitate was filtered, washed with water (4×100 mL) and vacuum dried over night to give the title compound (80.4 g) as an off white solid; MS (EI) 299, 301 (M)+.

Workup

  1. additionwas added
  2. stirringthe suspension was stirred vigorously for 4 hours
  3. filtrationThe precipitate was filtered
  4. washwashed with water (4×100 mL) and vacuum
  5. customdried over night

Sources & evidence

ORD record
ord-162cefa6db474a9d8fa7c0e886145401
Source dataset
uspto-grants-2012_07
Patent number
US08227491B2

Reaction notes

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