Potassium Hydroxide → 4-(4-bromo-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid

HRID 2392025Notes

Reaction equation

HRID 2392025 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:16][CH3:17])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[S:10][CH:11]=1.[OH-].[K+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:16][CH3:17])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[S:10][CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57826836methyl 4-(4-bromo-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 670660994-(4-bromo-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-(4-bromo-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (0.2 g, 0.63 mmol) in THF/H2O (5 mL/1 mL) was added KOH (0.15 g, 2.4 mmol). The reaction mixture was heated to 50° C. for 10 h and then concentrated and diluted with H2O (2 mL). The pH was adjusted to 6 with aqueous HCl. The mixture was extracted with DCM (3×5 mL) and the collected organic fractions were concentrated under vacuum to give crude 4-(4-bromo-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid, which was used directly without further purification. LC-MS (ES) m/z=302 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O (2 mL)
  3. extractionThe mixture was extracted with DCM (3×5 mL)
  4. concentrationthe collected organic fractions were concentrated under vacuum

Sources & evidence

ORD record
ord-409d7fcbc9c540d39a4a577c6706bd3b
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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