Tetra-n-butylammonium tribromide → HCID 59186000, compound

HRID 1671328Notes

Reaction equation

HRID 1671328 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([CH3:12])[CH:3]=1.[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[Br:13][CH:9]([CH3:10])[C:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH3:12])=[O:11]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 86638940HCID 86638940, compound

Product 1

HCID 59186000HCID 59186000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1-(6-chloro-4-methyl-pyridin-3-yl)-propan-1-one (0.25 g, 1.36 mmol) in DCM (6 ml) is added tetrabutylammonium tribromide (0.656 g, 1.36 mmol). The resulting orange solution is stirred at RT for 2 h (after 1 h a precipitate is observed). The reaction mixture is diluted with DCM and then quenched with water. The organic phase is separated and washed with water, dried over Na2SO4, filtered and evaporated. The crude product is purified on silica gel, using Heptane/EtOAc 99:1 to 80/20 gradient elution over 20 min to afford the title compound as a yellow oil; MS: m/z 261.9 [M+H]+.

Workup

  1. customquenched with water
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified on silica gel
  8. washto 80/20 gradient elution over 20 min

Sources & evidence

ORD record
ord-c264accb55da429bb353ae9eea62f70b
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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