Bromine → 2-(2-Benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromide

HRID 917669Notes

Reaction equation

HRID 917669 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:19])[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Br:20]Br>C(O)(=O)C>[Br-:20].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:19])[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[NH+:13]=3)[Br:20])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 24408BromineHCID 688850001-(1,3-benzodioxol-5-yl)-2-(6-methyl-2-pyridinyl)Ethanone

Product 1

HCID 865927612-(2-Benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromideYield 184.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 1-benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethanone (2 g, 7.83 mmol) in acetic acid (15 mL) was slowly added a solution of bromine (0.40 mL, 7.83 mmol, 1 equiv) in acetic acid (5 mL). The resulting reaction mixture was stirred at ambient temperature for I hour and then concentrated in vacuo. The residue was stirred in diethyl ether (20 mL) and methylene chloride (10 mL) over night. A light beige solid was filtered off, providing 2-(2-Benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromide (3.0 g, 92%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. stirringThe residue was stirred in diethyl ether (20 mL)
  4. waitmethylene chloride (10 mL) over night
  5. filtrationA light beige solid was filtered off

Sources & evidence

ORD record
ord-2c429c55ceaf47f29cd110520ff80787
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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