2-Acetylthiophene → 2-Acetyl-4,5-dichlorothiophene

HRID 844014Notes

Reaction equation

HRID 844014 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:8])[CH3:7].[Cl-:9].[Al+3].[Cl-:11].[Cl-].ClCl>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:9][C:4]1[CH:3]=[C:2]([C:6](=[O:8])[CH3:7])[S:1][C:5]=1[Cl:11]

Participants

7

Reactant 3

HCID 69202-AcetylthiopheneHCID 24526ChlorineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1488132-Acetyl-4,5-dichlorothiopheneYield 108.9%

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-Thiophen-2-yl-ethanone (5.0 grams, 40.0 mmole) in chloroform (50 ml) at 20° C. was added portionwise aluminum chloride (15.9 grams, 119.0 mmole). The mixture was stirred at 20° C. for 10 minutes and 1 M Cl2 in carbon tetrachloride (120 ml) was added dropwise. The mixture was stirred at room temperature for 30 minutes and diluted with methylene chloride (300 ml) and washed with 1 N sodium hydroxide and water and dried over magnesium sulfate and concentrated to give a solid (8.5 g). MW 195.07; MS (m/e) 196 (M++1).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. washwashed with 1 N sodium hydroxide and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a881c90d94a144ef950ac72d3e8de41c
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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