Phosphorus tribromide → 5-Benzyloxy-2-[2-(4-bromomethyl-phenyl)-ethyl]-2H-pyridazin-3-one

HRID 564166Notes

Reaction equation

HRID 564166 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[N: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([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[N: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

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 670075955-Benzyloxy-2-[2-(4-hydroxymethyl-phenyl)-ethyl]-2H-pyridazin-3-one

Product 1

HCID 670076305-Benzyloxy-2-[2-(4-bromomethyl-phenyl)-ethyl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 240 mg (0.71 mmol) 5-benzyloxy-2-[2-(4-hydroxymethyl-phenyl)-ethyl]-2H-pyridazin-3-one (example 21.1a) in 2.0 mL of DCM is added at 0° C. 134 μL (1.43 mmol) phosphorus tribromide. The mixture is stirred 4 h at RT, cooled to 0° C. and aqueous saturated NaHCO3-solution is added until pH >7. The layers are separated, the aqueous phase is extracted with DCM and the combined organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated.

Workup

  1. temperaturecooled to 0° C.
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with DCM
  4. washthe combined organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-e17ffe1c877e47c2bd5825e80cb66eae
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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