Thiophene, 2-nitro- → HCID 20026753, compound

HRID 1723166Notes

Reaction equation

HRID 1723166 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)([O-:3])=[O:2].[Cl-:9].[Al+3].[Cl-:11].[Cl-]>C(Cl)(Cl)Cl>[N+:1]([C:4]1[S:5][C:6]([Cl:11])=[C:7]([Cl:9])[CH:8]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11866Thiophene, 2-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 20026753HCID 20026753, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-nitrothiophene (10.0 g, 77.5 mmol) in 60 ml of chloroform is added aluminum chloride (6.0 g, 45.0 mmol). The mixture is cooled to 10° and chlorine gas is bubbled through for 3 hours at 25°-30°. Nitrogen gas is then bubbled through the mixture for 10 min., after which the mixture is poured into ice water and extracted with chloroform. The combined chloroform layers are washed with water and with brine and dried to give 2-nitro-4,5-dichlorothiophene.

Workup

  1. temperatureThe mixture is cooled to 10°
  2. customchlorine gas is bubbled through for 3 hours at 25°-30°
  3. customNitrogen gas is then bubbled through the mixture for 10 min.
  4. additionafter which the mixture is poured into ice water
  5. extractionextracted with chloroform
  6. washThe combined chloroform layers are washed with water and with brine
  7. customdried

Sources & evidence

ORD record
ord-c15632d8cc6f44068ec6f4b76e244ee1
Source dataset
uspto-grants-1989_08
Patent number
US04859699

Reaction notes

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