Sulfuric Acid → HCID 67491570, compound

HRID 880913Notes

Reaction equation

HRID 880913 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-0a764ab1033f449a8430b33d225821ef
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

Loading…