Benzyl Bromide → HCID 58171030, compound

HRID 337666Notes

Reaction equation

HRID 337666 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[NH:5][C:4](=[O:10])[CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 469162514-Bromo-5,6-dimethylpyridin-2-ol

Product 1

HCID 58171030HCID 58171030, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent2×

Procedure

4-Bromo-5,6-dimethyl-2(1H)-pyridinone (1 eq.), prepared according to the procedure described by McElroy, W. T.; DeShong, P. Organic Letters 2003, 5, 4779-4782, was suspended in benzene (0.13 M). To this was then added silver carbonate (0.6 eq.) and benzyl bromide (1.2 eq.) before the suspension was heated at 45° C. for 3 days in the dark. The reaction suspension was cooled to RT, diluted with benzene and filtered through a bed of celite. The filtrate was washed with sat. aq. NaHCO3, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification by way of column chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. filtrationfiltered through a bed of celite
  2. washThe filtrate was washed with sat. aq. NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification by way of column chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-0d4e7709a85d4158bd42dc103fcc5e71
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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