Benzyl Bromide → ethyl 1-benzyl-1H-pyrazole-4-carboxylate

HRID 928402Notes

Reaction equation

HRID 928402 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:9]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:10]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:2]([N:9]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 15237993ethyl 1-benzyl-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Bromomethyl-benzene (610 mg, 3.57 mmol) was suspended in Acetone (25 ml), ethyl 1H-pyrazole-4-carboxylate (500 mg, 3.57 mmol) and K2CO3 (2465 mg, 17.84 mmol) were added. The suspension was stirred 16 h at 50° C. The reaction mixture was filtrated and evaporated in vacuum to give the title compound which was used for the next step without further purification. HPLC/MS (Method A) RtA=1.82 min, MS [M+H]+=230.9.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customevaporated in vacuum

Sources & evidence

ORD record
ord-716679d359564f7ba9954bc592dabce4
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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