Phosphorus tribromide → HCID 67006807, compound

HRID 564129Notes

Reaction equation

HRID 564129 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=2)[C:9](=[O:23])[CH:8]=1.P(Br)(Br)[Br:28]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:28][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]3[CH:24]=[CH:25][CH:26]=[C:2]([F:1])[CH:3]=3)=[CH:8][C:9]2=[O:23])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 67006864HCID 67006864, compound

Product 1

HCID 67006807HCID 67006807, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 250 mg (0.71 mmol) 4-(3-fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 8.1a) 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 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 organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customto afford the product

Sources & evidence

ORD record
ord-d00866b9900d4912935a8241944f4e77
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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