Hydrochloric Acid → 4-bromo-1-(2-ethoxyethyl)-1H-pyrazole

HRID 928527Notes

Reaction equation

HRID 928527 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Cl.C(OCN1C2N=CN=C(C3C=NN([CH:30]([O:32][CH2:33][CH3:34])[CH3:31])C=3)C=2C=C1)(=O)C(C)(C)C>C(Cl)Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:31][CH2:30][O:32][CH2:33][CH3:34])[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 163754-BromopyrazoleHCID 57868870(4-(1-(1-Ethoxyethyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

Product 1

HCID 518921394-bromo-1-(2-ethoxyethyl)-1H-pyrazoleYield 108.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-bromopyrazole (21, 70.0 g, 0.476 mol) in CH2Cl2 (600 mL) was added a solution of 3.1 M HCl in dioxane (4 mL) and ethyl vinyl ether (18, 41 g, 0.569 mol, 1.2 equiv). The resulting reaction mixture was stirred at room temperature for 3 hrs. The reaction was quenched with aqueous NaHCO3 and the two layers were separated. The organic layer was washed with water, dried over Na2SO4, and concentrated under reduced pressure to dryness to afford 4-bromo-1-(ethoxyethyl)-1H-pyrazole (22, 113 g, 104.3 g theoretical, 97% yield) as an oily (GC purity: 89%), which was directly used in the subsequent reaction without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with aqueous NaHCO3
  3. customthe two layers were separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-c2538c7cb71e457c8a8aa86c37ba7527
Source dataset
uspto-grants-2016_03
Patent number
US09290506B2

Reaction notes

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