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

HRID 631910Notes

Reaction equation

HRID 631910 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([CH3:18])[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]([CH3:18])[N:8]=[N:7][C:6]=2[C:4]([OH:5])=[O:3])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 712664135-(4-bromo-phenyl)-1-methyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Product 1

HCID 712662725-(4-bromo-phenyl)-1-methyl-1H-[1,2,3]triazole-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(4-bromophenyl)-1-methyl-1H-[1,2,3]triazole-4-carboxylate (from step 3b, 2.0 g, 6.45 mmol) was dissolved in 30 mL of THF and 0.5N lithium hydroxide solution (15 mL) was added. The mixture was stirred at room temperature for 10 hrs and solvents were evaporated. The residue was dissolved in water (30 mL) and filtered. The filtrate was treated with hydrochloric acid (2N, 4 mL). The white solid was filtered and dried to give 5-(4-bromo-phenyl)-1-methyl-1H-[1,2,3]triazole-4-carboxylic acid (1.82 g, 100% yield). LC-MS calcd for C10H8BrN3O2 (m/e) 283.0, obsd 282.0 (M−H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.89 (s, 3H), 7.50 (d, J=8.4 Hz, 2H), 7.75 (d, J=8.4 Hz, 2H), 12.95 (br s, 1H).

Workup

  1. customsolvents were evaporated
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. filtrationfiltered
  4. additionThe filtrate was treated with hydrochloric acid (2N, 4 mL)
  5. filtrationThe white solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-ddb4ce99c65349c3abbb3a5e4a07ef81
Source dataset
uspto-grants-2016_04
Patent number
US09321738B2

Reaction notes

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