Phosphorus tribromide → HCID 86680630, compound

HRID 1497465Notes

Reaction equation

HRID 1497465 reaction equation
O[CH:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:3][CH3:4].P(Br)(Br)[Br:20]>C(Cl)(Cl)Cl>[Br:20][CH:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 86680629HCID 86680629, compound

Product 1

HCID 86680630HCID 86680630, compoundYield 145.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(6-(1-hydroxypropyl)pyridin-3-yl)benzonitrile (0.10 g, 0.21 mmol) in chloroform (4 mL) was added PBr3 (0.34 g, 0.63 mmol) at 0-5° C. This temperature was maintained for 15 min, was slowly allowed to rt and was then maintained at rt for another 90 min. The contents were diluted with chloroform (100 mL) and washed with bicarbonate solution (2×30 mL). The organic layer was separated, dried over sodium sulphate and evaporated to provide 4-(6-(1-bromopropyl)pyridin-3-yl)benzonitrile (92 mg, 73% yield).

Workup

  1. temperatureThis temperature was maintained for 15 min
  2. customwas slowly allowed to rt
  3. washwashed with bicarbonate solution (2×30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-b37f250c4d2740178e820df4d2f4a737
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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