Bromine → HCID 178520129, compound

HRID 1776892Notes

Reaction equation

HRID 1776892 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[C:5]([O:8]C)=[N:6][CH:7]=1.[Br:13]Br>Br>[Br:13][CH2:11][C:10]([C:4]1[C:5]([OH:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 712951831-(5-Bromo-2-methoxypyridin-3-yl)ethan-1-one

Product 1

HCID 178520129HCID 178520129, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

To a solution of 1-(5-bromo-2-methoxypyridin-3-yl)ethanone (2.0 g, 8.69 mmol) in HBr (20 mL, HOAc solution), Br2 (1.4 g, 8.76 mmol) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. Then the reaction mixture was filtered to collect the HBr salt. The solid was suspended with Na2CO3 solution, extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 2-bromo-1-(5-bromo-2-hydroxypyridin-3-yl)ethanone (2.0 g, yield: 74%). 1H-NMR (DMSO, 400 MHz) δ 12.83 (br s, 1H), 8.11˜8.13 (m, 2H), 4.85 (s, 2H). MS (M+H)+: 295.

Workup

  1. filtrationThen the reaction mixture was filtered
  2. customto collect the HBr salt
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6066a1b5e0814d8289b6796459f85b3e
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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