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

HRID 1425737Notes

Reaction equation

HRID 1425737 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][C:19]=2[CH3:26])=[O:17])[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:29]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][Br:29])=[CH:20][C:19]=2[CH3:26])=[O:17])[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 866955374-Benzyloxy-1-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Product 1

HCID 866955384-Benzyloxy-1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzyloxy-1-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one (preparation 1c, 1.10 g, 3.03 mmol) in CH2Cl2 (20 mL) is added slowly phosphorus tribromide (199 μL, 2.12 mmol) at 0° C. The cooling bath is removed and the mixture is stirred for 1 h at room temperature. After cooling, the reaction mixture is quenched with aqueous NaHCO3 solution and extracted with CH2Cl2. The organic layer is washed with water, dried over MgSO4, and concentrated under reduced pressure.

Workup

  1. customThe cooling bath is removed
  2. temperatureAfter cooling
  3. customthe reaction mixture is quenched with aqueous NaHCO3 solution
  4. extractionextracted with CH2Cl2
  5. washThe organic layer is washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9877afe63ea7496e88d9c26ab36677c5
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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