Phosphorus tribromide → HCID 86680622, compound

HRID 1497451Notes

Reaction equation

HRID 1497451 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([CH:12](O)[CH3:13])=[N:10][CH:11]=2)=[CH:2]1.P(Br)(Br)[Br:16]>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(=O)(O)[O-]>[Br:16][CH:12]([C:9]1[CH:8]=[CH:7][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[CH:11][N:10]=1)[CH3:13]

Participants

6

Reactant 2

HCID 24614Phosphorus tribromideHCID 86680621HCID 86680621, compound

Product 1

HCID 86680622HCID 86680622, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 769Bicarbonate IonSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 1-(5-(furan-3-yl)pyridin-2-yl)ethanol (0.075 g, 0.403 mmol) in chloroform (5 ml) was added PBr3 (0.321 g, 1.209 mmol), at 0-5° C., the reaction maintained at the same temperature for 15 min, the reaction was slowly warmed to rt and was maintained at rt for another 2 h. The contents were diluted with ethyl acetate (100 mL), bicarbonate solution (10 mL) was added, the organic layer was separated, the organic layer dried over sodium sulphate and distilled to provide 2-(1-bromoethyl)-5-(furan-3-yl)pyridine (0.075 g, 75% yield). LC-MS m/z calcd for [M+H]+ 253.99. found 254.0.

Workup

  1. temperaturethe reaction was slowly warmed to rt
  2. temperaturewas maintained at rt for another 2 h
  3. additionwas added
  4. customthe organic layer was separated
  5. dry with materialthe organic layer dried over sodium sulphate
  6. distillationdistilled

Sources & evidence

ORD record
ord-18e0372e89e54c21bb804d76265cc5cf
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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