1-Bromo-2-Chloroethane → 4-Bromo-1-(2-chloroethyl)-1H-pyrazole

HRID 2366841Notes

Reaction equation

HRID 2366841 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][CH2:15][Cl:16]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:14][CH2:15][Cl:16])[CH:6]=1

Participants

5

Conditions

Temperature
60 °C

Procedure

4-bromopyrazole (700 mg, 4.76 mmol, available from Aldrich), cesium carbonate (2328 mg, 7.14 mmol) and 1-bromo-2-chloroethane (0.592 ml, 7.14 mmol, available from Acros) were suspended in N,N-Dimethylformamide (DMF) (14 ml) and heated to 60° C. under microwave conditions in an Emrys Optimiser for 1 hour. The mixture was partitioned between water (20 ml) and ethyl acetate (60 ml). The aqueous layer was run off and the organic washed (water 3×10 ml), brine (10 ml)), dried (magnesium sulfate) and evaporated to dryness to give the desired product (868 mg).

Workup

  1. customThe mixture was partitioned between water (20 ml) and ethyl acetate (60 ml)
  2. washthe organic washed (water 3×10 ml), brine (10 ml)),
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d0f3502d0f0544f7b6bac75fc07e386c
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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