1,2-Dibromoethane → Dimethyl 1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylate

HRID 399431Notes

Reaction equation

HRID 399431 reaction equation
[NH:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.C([O-])([O-])=O.[K+].[K+].[Br:20][CH2:21][CH2:22]Br>C(#N)C>[Br:20][CH2:21][CH2:22][N:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14844913,5-dimethyl 1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 1484510Dimethyl 1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of this ester (5.0 g, 27.2 mmol) in 150 ml of anhydrous acetonitrile was treated with K2CO3 (5.2 g, 40.0 mmol) and 1,2-dibromoethane (25.0 ml, 291 mmol). The resulting mixture was heated to reflux under argon. After 25 min the reaction suspension was cooled, filtered and the filtrate evaporated to dryness at reduced pressure and placed on a high vacuum line for 12 h. The resulting white solid was recrystalized from hexane to give 3-2 as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux under argon
  3. temperatureAfter 25 min the reaction suspension was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness at reduced pressure
  6. customThe resulting white solid was recrystalized from hexane

Sources & evidence

ORD record
ord-74ed1fc8ec464cc690ae702b54bca921
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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