Sulfuric Acid → HCID 67491570, compound

HRID 711042Notes

Reaction equation

HRID 711042 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-f5bcf2560de2409fb2193fa926474ef0
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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