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

HRID 564103Notes

Reaction equation

HRID 564103 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:27]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:27])=[CH:19][CH:18]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 670067844-Benzyloxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 670065714-Benzyloxy-1-[2-(4-bromomethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.00 g (8.95 mmol) 4-benzyloxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (preparation 2a) in 30 mL of DCM is added 1.26 mL (13.4 mmol) phosphorus tribromide at 0° C. The cooling bath is removed, the mixture is stirred 2 h at RT and is diluted with half saturated aqueous NaHCO3-solution. The layers are separated and the aqueous layer is washed 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 cooling bath is removed
  2. additionis diluted with half saturated aqueous NaHCO3-solution
  3. customThe layers are separated
  4. washthe aqueous layer is washed three times with DCM
  5. dry with materialThe combined organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. customto afford the product

Sources & evidence

ORD record
ord-4aad5ff7220c49a2acfa4b0c8e94eb09
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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