Phosphorus tribromide → 1-[2-(4-bromomethylphenyl)-ethyl]-4-(furan-3-ylmethoxy)-1H-pyridin-2-one

HRID 564117Notes

Reaction equation

HRID 564117 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=3)[C:10](=[O:24])[CH:9]=2)=[CH:2]1.P(Br)(Br)[Br:26]>C(Cl)Cl>[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:3]3[CH:4]=[CH:5][O:1][CH:2]=3)=[CH:9][C:10]2=[O:24])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 670075744-(Furan-3-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 670069631-[2-(4-bromomethylphenyl)-ethyl]-4-(furan-3-ylmethoxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 220 mg (0.68 mmol) 4-(furan-3-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 5.1a) in 8.0 mL of DCM is added at 0° C. 44 μL (0.47 mmol) phosphorus tribromide. After warming to RT, the mixture is stirred 2 h at RT and is diluted with ice water. 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-1f24ffce4a2b4d2490dbfa1d97f9b1e1
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

Loading…