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

HRID 564111Notes

Reaction equation

HRID 564111 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.P(Br)(Br)[Br:27]>C(Cl)Cl.C(OC)(C)(C)C>[Br:27][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 670066931-[2-(4-hydroxymethylphenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 670077401-[2-(4-Bromomethyl-phenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To 1.20 g (3.57 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one (example 3.1a) in 25 mL of DCM is added at 0° C. 0.24 mL (2.50 mmol) phosphorus tribromide. After warming to RT, the mixture is stirred 2 h at RT and is diluted with 30 mL tertbutylmethylether. The precipitate is collected and dried.

Workup

  1. customThe precipitate is collected
  2. customdried

Sources & evidence

ORD record
ord-620830f66267463aa1fd2d7bd7046077
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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