Hydrochloric Acid → 2-(4-chlorophenyl)thiophene

HRID 1723168Notes

Reaction equation

HRID 1723168 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[S:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[OH-].[Na+]>O.C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 8030ThiopheneHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 119716552-(4-chlorophenyl)thiophene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Chloroaniline (4.0 g, 31.4 mmol) is added to 4 ml of acetic acid and heated until all solid is dissolved. The solution is cooled to 5° and 5.2 ml of conc. HCl is added, followed by the dropwise addition of sodium nitrite (2.16 g, 31.4 mmol) in 32 ml of water. After addition is complete, the mixture is stirred at 5° for 1 hour. Thiophene (2.64 g, 2.5 ml, 31.4 mmol) in 25 ml of carbon tetrachloride is added to the mixture, followed by the dropwise addition of 25% aq. NaOH (ca. 6.8 ml). After 1 hour, the mixture is poured into water and extracted with chloroform, and the combined extracts are washed with brine, dried and stripped of solvent. The black residue is distilled at ca. 120° 0.35 mm to give 2-(4-chlorophenyl)thiophene, a yellow solid.

Workup

  1. temperatureheated until all solid
  2. dissolutionis dissolved
  3. temperatureThe solution is cooled to 5°
  4. additionAfter addition
  5. waitAfter 1 hour
  6. extractionextracted with chloroform
  7. washthe combined extracts are washed with brine
  8. customdried
  9. distillationThe black residue is distilled at ca. 120° 0.35 mm

Sources & evidence

ORD record
ord-08ab1c466ec447b88edc5f0d6288ee08
Source dataset
uspto-grants-1989_08
Patent number
US04859699

Reaction notes

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