1-Bromo-4-chlorobutane → HCID 21216767, compound

HRID 1586397Notes

Reaction equation

HRID 1586397 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([OH:14])[CH:11]=[C:10]([CH3:15])[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][Cl:21]>C(=O)([O-])[O-].[Ag+2].C1(C)C=CC=CC=1>[ClH:21].[Cl:21][CH2:20][CH2:19][CH2:18][CH2:17][O:14][C:12]1[CH:11]=[C:10]([CH3:15])[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 813641-Bromo-4-chlorobutaneHCID 178428993HCID 178428993, compound

Product 1

HCID 21216767HCID 21216767, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2.5 g of 2-(4-fluorophenyl)-4-hydroxy-6-methylpyridine, 3.16 g of 1-bromo-4-chlorobutane, 1.7 g of silver carbonate, and 100 ml of toluene was refluxed for 40 hours. This reaction mixture was filtered to remove insolubles and the filtrate was concentrated. The residue was purified with silica gel column chromatography to provide 1.45 g of the title compound as white crystals.

Workup

  1. temperaturewas refluxed for 40 hours
  2. filtrationThis reaction mixture was filtered
  3. customto remove insolubles
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-5d9c3db224394acd8419260413822e17
Source dataset
uspto-grants-1999_08
Patent number
US05945426

Reaction notes

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