Hydrochloric Acid → 3-Bromo-5-cyclopenten-1-ylpyridine

HRID 1767765Notes

Reaction equation

HRID 1767765 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.Cl.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 161095341-(5-Bromopyridin-3-yl)cyclopentanol

Product 1

HCID 161095213-Bromo-5-cyclopenten-1-ylpyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(5-bromopyridin-3-yl)cyclopentanol (8) (1.7 g, 11.3 mmol) in 50 ml of toluene containing 5 ml of concentrated hydrochloric acid is heated at 120° C. for 12 hours with continuous carrying away of the water formed. The mixture is then poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases are washed with water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 60/40). The title product is obtained in the form of a beige solid (1.65 g).

Workup

  1. customformed
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialwith a saturated aqueous sodium chloride solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 60/40)

Sources & evidence

ORD record
ord-c2c5a0e12bce4d1294198e55ef468d0c
Source dataset
uspto-grants-2007_06
Patent number
US07235568B2

Reaction notes

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