Phosphorus tribromide → 1-[2-(4-Bromomethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

HRID 564159Notes

Reaction equation

HRID 564159 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.P(Br)(Br)[Br:27].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:27][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 670073171-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

Product 1

HCID 670066581-[2-(4-Bromomethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 150 mg (0.45 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one (example 18.1a) in 2.0 mL of DCM is added at 0° C. 21 μL (0.23 mmol) phosphorus tribromide. The mixture is stirred 2 h at RT and is then added to aqueous 5% NaHCO3-solution. The layers are separated, the aqueous phase is extracted with DCM. The combined organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated to afford the product.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with DCM
  3. washThe combined organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customto afford the product

Sources & evidence

ORD record
ord-5173d15553f64107be5b637eaea21d87
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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