Thionyl Chloride → 7-Chloro-2-(5-chloromethylbenzofuran-2-yl)quinoline

HRID 2258516Notes

Reaction equation

HRID 2258516 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH2:21][Cl:25])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 229221977-Chloro-2-(5-hydroxymethylbenzofuran-2-yl)quinoline

Product 1

HCID 229221267-Chloro-2-(5-chloromethylbenzofuran-2-yl)quinolineYield 110.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7-chloro-2-(5-hydroxymethylbenzofuran-2-yl)quinoline (0.40 g) and thionyl chloride (0.30 g) in chloroform (20 ml) was stirred under reflux for 1 hour. After being cooled, the resulting mixture was adjusted to pH 7 with aqueous sodium hydrogen carbonate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 7-chloro-2-(5-chloromethylbenzofuran-2-yl)quinoline (0.47 g).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter being cooled
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6cc55b91192d47e899a703bab066dc0d
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

Loading…