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

HRID 564121Notes

Reaction equation

HRID 564121 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=2)[C:10](=[O:24])[CH:9]=1.P(Br)(Br)[Br:26]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:26][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][N:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:9][C:10]2=[O:24])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 670074744-(Furan-2-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 670068811-[2-(4-Bromomethyl-phenyl)-ethyl]-4-(furan-2-ylmethoxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 80 mg (0.25 mmol) 4-(furan-2-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 6.1a) in 3.0 mL of DCM is added at 0° C. 35 μL (0.37 mmol) phosphorus tribromide. After warming to RT, the mixture is stirred 2 h at RT and is diluted with half saturated aqueous NaHCO3-solution. The layers are separated, the aqueous phase is extracted three times with DCM/MeOH. 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/MeOH
  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-67dd4b51ce0444bea6bbc1af7778ae6c
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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