Ethyl bromoacetate → ethyl 3,5-dichloro-1H-pyrazole-1-acetate

HRID 2043739Notes

Reaction equation

HRID 2043739 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([Cl:7])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:6]=[C:5]([Cl:7])[N:4]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:3]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 203280693,5-dichloro-1H-pyrazole2×

Product 1

HCID 67463975ethyl 3,5-dichloro-1H-pyrazole-1-acetateYield 94.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3,5-dichloro-1H-pyrazole (690 mg, 5.0 mmol) (i.e. the product of Example 12, Step D), potassium carbonate (3 g, 21 mmol) in N,N-dimethylformamide (10 mL) was treated with ethyl bromoacetate (1.0 mL, 9.0 mmol) and stirred at ambient temperature for 12 h. The suspension was diluted with ethyl acetate, washed with water, and dried over MgSO4. The reaction mixture was then concentrated under reduced pressure giving 1.05 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd47032d9e9d4578891876cca7350dcc
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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