2-Chloropyridine → HCID 89581271, compound

HRID 1501106Notes

Reaction equation

HRID 1501106 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1.Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[K+]>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79772-ChloropyridineHCID 14797Potassium HydroxideHCID 953521-(4-Bromophenyl)ethanol

Product 1

HCID 89581271HCID 89581271, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent

Procedure

A solution of 1-(4-bromophenyl)ethanol (2.0 g, 10.0 mmol), 2-chloropyridine (1237 mg, 11.0 mmol), potassium hydroxide (1839 mg, 32.8 mmol) and 18-crown-6 (132 mg, 0.5 mmol) in toluene (40 mL) was stirred at reflux for 3 hrs. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=20:1) to give 2-(1-(4-bromophenyl)ethoxy)pyridine as a white solid (2.6 g, 94%). LRMS (M+H+) m/z: calcd 277.01. found 277.

Workup

  1. temperatureat reflux for 3 hrs
  2. concentrationThe mixture was concentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-d8ca7fef128f4a53b6a1b4c5068300e1
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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