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

HRID 564065Notes

Reaction equation

HRID 564065 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][CH:19]=2)=[O:17])[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:28]>C(Cl)Cl.C1COCC1>[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:28])=[CH:20][CH:19]=2)=[O:17])[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 670068424-Benzyloxy-1-[2-(4-hydroxymethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Product 1

HCID 580428824-Benzyloxy-1-[2-(4-bromomethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3.00 g (8.59 mmol) 4-benzyloxy-1-[2-(4-hydroxymethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one (preparation 15b) in 20 mL of DCM and 20 mL THF is added 0.81 mL (8.59 mmol) phosphorus tribromide at 0° C. The cooling bath is removed and the mixture is stirred 1 h at RT in an ultrasound bath.

Workup

  1. customThe cooling bath is removed

Sources & evidence

ORD record
ord-57b18864eb434029ac4acc4ef573e485
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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