1-Bromo-4-chlorobutane → HCID 15524186, compound

HRID 635890Notes

Reaction equation

HRID 635890 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>[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 15524186HCID 15524186, compoundYield 40.1%

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-27deb012ad3a4c2cbbc4c3c08c6b1a2a
Source dataset
uspto-grants-2001_02
Patent number
US06191149B1

Reaction notes

Loading…