Hydrochloric Acid → 2-Chloro-5-nitrophenyl 3-chloro-2-thienyl ketone

HRID 48965

Reaction equation

HRID 48965 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.[Cl:11][C:12]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=1[C:14](Cl)=[O:15].Cl>C(Cl)Cl>[Cl:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:14]([C:13]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:12]=1[Cl:11])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 870173-ChlorothiopheneHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 206342582-Chloro-5-nitrophenyl 3-chloro-2-thienyl ketoneYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of aluminum chloride (1.33 g, 0.0102 mol) and methylene chloride is added 3-chlorothiophene (1.21 g, 0.0102 mol) dropwise. The resultant mixture is stirred 30 minutes and treated with a solution of 2-chloro-5-nitrobenzoyl chloride (2.20 g, 0.0100 mol) in methylene chloride. The resultant mixture is stirred overnight at room temperature, poured into ice, acidified with concentrated hydrochloric acid and extracted twice with methylene chloride. The combined organic layers are washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a brown oil. Trituration with ether affords the title compound as a brown solid (1.33 g, 44.0%, mp 114-116° C.) which is identified by NMR spectral analysis.

Workup

  1. additionpoured into ice
  2. extractionextracted twice with methylene chloride
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo to a brown oil

Sources & evidence

ORD record
ord-b88bd5e8fc374d8eaafcec445099e04a
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Linked notes

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