Phosphorus tribromide → HCID 67006550, compound

HRID 564125Notes

Reaction equation

HRID 564125 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([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:4][CH:3]=1.P(Br)(Br)[Br:28]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:28][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:5]3[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][C:10]2=[O:24])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 67006610HCID 67006610, compound

Product 1

HCID 67006550HCID 67006550, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 300 mg (0.85 mmol) 4-(4-fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 7.1a) in 5.0 mL of DCM is added 120 μL (1.27 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-90df8687bd434d359d819d3be9cb0286
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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