Hydrogen Bromide → 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one

HRID 1047176Notes

Reaction equation

HRID 1047176 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=[O:9])[CH3:8])[CH:4]=[N:3]1.[BrH:10].BrBr>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:10][CH2:8][C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 35969391-(1-methyl-1H-pyrazol-4-yl)ethan-1-one

Product 1

HCID 431441522-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(1-methyl-1H-pyrazol-4-yl)ethanone (0.602 g, 4.85 mmol) in chloroform (20 mL) and of 33% HBr in acetic acid (3.92 mg, 0.05 mmol) was added dropwise a chloroform solution containing Br2 (0.262 mL, 5.09 mmol) via an addition funnel. The reaction mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. The crude solid was triturated in ethyl acetate, filtered, washed and dried in vacuo. The free base was obtained by triturating the product in 5% NaHCO3 for 2 h. The solid that formed were collected by filtration, washed with water and isopropyl alcohol and then dried in vacuo. Isolation gave 874 mg of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude solid was triturated in ethyl acetate
  3. filtrationfiltered
  4. washwashed
  5. customdried in vacuo
  6. customThe free base was obtained
  7. customby triturating the product in 5% NaHCO3 for 2 h
  8. customThe solid that formed
  9. filtrationwere collected by filtration
  10. washwashed with water and isopropyl alcohol
  11. customdried in vacuo

Sources & evidence

ORD record
ord-620cd5c12e4643b6a007622b08c1974c
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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