Ethyl diazoacetate → 1H-Pyrazole-3-carboxylic acid, 5-(trifluoromethyl)-, ethyl ester

HRID 1053992Notes

Reaction equation

HRID 1053992 reaction equation
Br[C:2]([C:4]([F:7])([F:6])[F:5])=[CH2:3].[N+:8](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-:9]>C(OCC)C>[CH2:14]([O:13][C:11]([C:10]1[CH:3]=[C:2]([C:4]([F:7])([F:6])[F:5])[NH:9][N:8]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-

Product 1

HCID 27269191H-Pyrazole-3-carboxylic acid, 5-(trifluoromethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-bromo-3,3,3-trifluoro-1-propene (1 g, 5.716 mmol) in diethyl ether (2 ml) cooled with ice-bath under N2 atmosphere a solution of ethyl diazoacetate (1.06 ml, 8.574 mmol) in diethyl ether (3 ml) was added drop wise. The mixture was warmed to RT and then refluxed for 3 hours. The volatiles were removed under vacuum. Vacuum distillation provided the title compound.

Workup

  1. additionwas added drop wise
  2. temperaturerefluxed for 3 hours
  3. customThe volatiles were removed under vacuum
  4. distillationVacuum distillation

Sources & evidence

ORD record
ord-9d40991fb0d14127883cb0d49b25a8cd
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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