Phosphorus tribromide → 1-[2-(4-bromomethyl-phenyl)ethyl]-4-(2-fluoro-benzyloxy)-1H-pyridin-2-one

HRID 564133Notes

Reaction equation

HRID 564133 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=2)[C:8](=[O:22])[CH:7]=1.P(Br)(Br)[Br:28]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:28][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][N:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[F:1])=[CH:7][C:8]2=[O:22])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 670072854-(2-Fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 670066651-[2-(4-bromomethyl-phenyl)ethyl]-4-(2-fluoro-benzyloxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 250 mg (0.71 mmol) 4-(2-fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 9.1a) in 4.0 mL of DCM is added 100 μL (1.06 mmol) phosphorus tribromide. The mixture is stirred 2 h at RT and is diluted with half saturated aqueous NaHCO3-solution. The layers are separated and the aqueous phase is extracted three times with DCM. The combined organic phase is 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 three times with DCM
  3. dry with materialThe combined organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customto afford the product

Sources & evidence

ORD record
ord-efe57644ab5c49a6a227981e0b93004b
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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