Lithium Hydroxide → 5-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid

HRID 631909Notes

Reaction equation

HRID 631909 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:18])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Li+]>C1COCC1>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[N:9]=[N:8][N:7]([CH3:18])[C:6]=2[C:4]([OH:5])=[O:3])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 712664555-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Product 1

HCID 712662515-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (1.2 g, 3.87 mmol) was dissolved in THF (15 mL) and lithium hydroxide solution (0.5 N, 10 mL) was added. The mixture was stirred at room temperature for 3 hrs. TLC indicated complete consumption of the starting material. The mixture was concentrated and the residue was dissolved in water (20 mL) and filtered. The filtrate was acidified with 2N hydrochloric acid (3 mL). The white solid was filtered and dried to give 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid as a white solid (1.03 g, 94.4% yield). m.p. 209-210° C.; LC-MS calcd for C10H8BrN3O2 (m/e) 283.0, obsd 284.0 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 4.26 (s, 3H), 7.66-7.72 (m, 4H), 14.20 (br s, 1H).

Workup

  1. customconsumption of the starting material
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. filtrationfiltered
  5. filtrationThe white solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-536bca20fd074e549cd650e34f873663
Source dataset
uspto-grants-2016_04
Patent number
US09321738B2

Reaction notes

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