Diethyl Ether → 4-(3-Bromopropyl)pyridine

HRID 1645222Notes

Reaction equation

HRID 1645222 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]O)=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>C(Cl)(Cl)Cl>[Br:12][CH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 729234-Pyridinepropanol

Product 1

HCID 127470564-(3-Bromopropyl)pyridineYield 111.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.0 g of 4-pyridinepropanol was dissolved in 90 ml of chloroform, 9.4 g of carbon tetrabromide and 7.5 g of triphenylphosphine was added under ice cooling, and the mixture was stirred for 2 hours. Ether was added to the reaction solution, and the mixture was extracted with 1N hydrochloric acid, and then the aqueous layer was washed with ether. The aqueous layer was adjusted to be basic with 6N sodium hydroxide, and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give 4.86 g of 4-(3-bromopropyl)pyridine.

Workup

  1. extractionthe mixture was extracted with 1N hydrochloric acid
  2. washthe aqueous layer was washed with ether
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-35cb1e605161459b95d4070dd70f1b34
Source dataset
uspto-grants-2012_02
Patent number
US08124744B2

Reaction notes

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