Ethyl Acetate → HCID 64430376, compound

HRID 531432Notes

Reaction equation

HRID 531432 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br.C(OCC)(=O)C>CN(C=O)C.CCCCCC>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 770224-Iodopyrazole

Product 1

HCID 64430376HCID 64430376, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution 4-iodo-1H-pyrazole (1.5 g, 7.7 mmol) in DMF (15 ml) was added potassium carbonate (3.2 g, 23.2 mmol) followed by drop wise addition of 2-fluoro benzyl bromide (2.56 g, 8.5 mmol) and stirred the reaction at RT for 15 h. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was diluted with ice water (150 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 2.25 g (96.56% yield) of 1-(2-fluorobenzyl)-4-iodo-1H-pyrazole.

Workup

  1. customthe reaction at RT for 15 h
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20d84174bf2c4cb58a56ba19a3826e11
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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