2-Bromopyridine → 2-(5-Chloropent-1-ynyl)pyridine

HRID 334777Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13]>>[Cl:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 843081-Pentyne, 5-chloro-

Product 1

HCID 665985572-(5-Chloropent-1-ynyl)pyridineYield 61%

Procedure

The title compound was prepared in accordance with the general method of Example 190(F), from 2-bromopyridine (948 mg, 6.0 mmol) and 5-chloropent-1-yne (620 mg, 6.0 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: from 100/0 to 80/20 as eluent) to afford 655 mg of 2-(5-chloropent-1-ynyl)pyridine as a yellow oil (Yield: 61%).

Workup

customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: from 100/0 to 80/20 as eluent)

Sources & evidence

ORD record: ord-be5754d4b9bd49b2a9477925011c81d3
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883826B2

Reaction notes

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