Sulfuric Acid → HCID 67491570, compound

HRID 537116Notes

Reaction equation

HRID 537116 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][NH:9][N:8]=1.[C:17](O)([CH2:20][CH3:21])([CH3:19])[CH3:18]>C(OCC)(=O)C>[Br:6][C:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]([C:17]([CH2:20][CH3:21])([CH3:19])[CH3:18])[N:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 64052-Methyl-2-butanolHCID 178469910HCID 178469910, compound

Product 1

HCID 67491570HCID 67491570, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Concentrated sulfuric acid (0.45 mL, 4.8 mmol) was added to a mixture of ethyl 3-bromo-1H-pyrazole-4-carboxylate (1.0 g, 4.6 mmol) and tert-amyl alcohol (3.0 mL, 27 mmol). The reaction was heated to 100° C. for 2.5 hours. The reaction was then cooled to room temperature and left stirring overnight. The reaction was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield ethyl 3-bromo-1-tert-pentyl-1H-pyrazole-4-carboxylate (1.3 g) as a crude brown oil.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. waitleft
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9dfa224de3d94cb3a04433684100f809
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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