Sodium Hydroxide → 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

HRID 1480138Notes

Reaction equation

HRID 1480138 reaction equation
[Br:1][C:2]1[C:3]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([C:8]#N)=[N:6][CH:7]=1.N([O-])=[O:17].[Na+].[OH-:20].[Na+]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:3]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([C:8]([OH:17])=[O:20])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 902033795-Bromo-4-(2,2,2-trifluoroethoxy)picolinonitrile

Product 1

HCID 902041215-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carbonitrile (Example 78c, 1 g, 3.56 mmol) in sulfuric acid 97% (5 ml) was stirred at 120° C. for 2 h and a 6.0M aqueous solution of sodium nitrite (2.08 ml, 12.5 mmol, Eq: 3.5) was then slowly added to it at r.t. The resulting reaction mixture was stirred at room temperature for 30 minutes and stirred at 80° C. for 1 hour. The reaction was diluted by addition of 20 gr of ice and the pH was adjusted to 1-2 by addition of sodium hydroxide pellets by portions. A precipitate formed and was filtered off, dried under high vacuum to yield the title compound (1.02 g, 95%) as a white solid. MS (ESI, m/z): 300.2 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred at 80° C. for 1 hour
  3. customA precipitate formed
  4. filtrationwas filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-236fb1b146394a70ad5615e1ea1f6386
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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