Bromine → 5-Bromo-2-methoxypyridine-3-carboxylic acid

HRID 1776889Notes

Reaction equation

HRID 1776889 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[Br:12]Br>O>[Br:12][C:9]1[CH:10]=[N:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 7080932-Methoxynicotinic acid

Product 1

HCID 143717285-Bromo-2-methoxypyridine-3-carboxylic acidYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methoxynicotinic acid (20 g, 130.60 mmol) in H2O (1500 mL), Br2 (20 mL, 375.45 mmol) was added at room temperature. The mixture was stirred at room temperature overnight. The reaction mixture was filtered, washed with water and dried to provide 5-bromo-2-methoxynicotinic acid (25 g, yield: 82%). 1H-NMR (DMSO, 400 MHz) δ 13.33 (br s, 1H), 8.47 (d, J=2.4 Hz, 1H), 8.21 (d, J=2.4 Hz, 1H), 3.90 (s, 3H). MS (M+H)+: 232/234.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-dfa4bdd507f14c60b5f8f08df7535f90
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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