Hydrogen Bromide → HCID 87870279, compound

HRID 1178550Notes

Reaction equation

HRID 1178550 reaction equation
[CH3:1][C:2]1[C:7]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:5]=[C:4]([CH3:12])[N:3]=1.[BrH:13].BrBr>C(O)(=O)C>[Br:13][CH:9]([CH3:10])[C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([CH3:12])=[CH:5][CH:6]=1)=[O:11]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 69524486HCID 69524486, compound

Product 1

HCID 87870279HCID 87870279, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution 1-(2,6-dimethl-pyridine-3-yl)-propan-1-one (0.3 g, 1.8 mmol) in 30% by weight solution of hydrogen bromide in acetic acid (3 ml) was added dropwise (0.29 g, 1.8 mmol) of Bromine. The reaction was allowed to warm to room temperature with stirring for 2h. The mixture was then concentrated in vacuo and the resulting crude material neutralized using saturated sodium carbonate solution. The mixture was extracted twice with dichloromethane and the combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. Yield: 400 mg (92%). 1H NMR (300 MHz, CDCl3), •1.88 (d, CH3, 3H), 2.64 (s, CH3, 3H), 2.76 (s, CH3, 3H), 5.12 (q, CH, 1H), 7.14 (d, Ar, 1 H,), 7.93 (d, Ar, 1 H).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionThe mixture was extracted twice with dichloromethane
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ead7bd917bb746d182d4e235b968fbad
Source dataset
uspto-grants-2007_10
Patent number
US07276526B2

Reaction notes

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