Phosphorus tribromide → HCID 86680609, compound

HRID 1497433Notes

Reaction equation

HRID 1497433 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH:15](O)[CH2:16][CH3:17])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.P(Br)(Br)[Br:20]>C(Cl)(Cl)Cl.O>[Br:20][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:14][N:13]=1)[CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 86680608HCID 86680608, compound

Product 1

HCID 86680609HCID 86680609, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(5-(3-methoxyphenyl)pyridin-2-yl)propan-1-ol (0.45 g, 1.8 mmol) in chloroform (5 mL) was added PBr3 (1.5 g, 5.55 mmol) at 0-5° C., the reaction was maintained at the same temperature for 1 h, and then the reaction was slowly warmed to rt and maintained at this temperature for 1 h. The contents were diluted with water (75 mL) and chloroform (100 mL) and the layers were separated. The organic layer was washed with bicarbonate solution (2×30 mL), dried over sodium sulphate and distilled to get the crude product. The non-polar impurity was removed by pentane washings (2×7 mL) to provide 2-(1-bromopropyl)-5-(3-methoxyphenyl)pyridine (0.45 g, crude). LC-MS m/z calcd for [M+H]+ 306.04. found 306.0.

Workup

  1. temperaturethe reaction was maintained at the same temperature for 1 h
  2. temperaturemaintained at this temperature for 1 h
  3. customthe layers were separated
  4. washThe organic layer was washed with bicarbonate solution (2×30 mL)
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled
  7. customto get the crude product
  8. customThe non-polar impurity was removed by pentane washings (2×7 mL)

Sources & evidence

ORD record
ord-680010e9387a45218032444ef8ec38dc
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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