Chlorobenzene → HCID 86736353, compound

HRID 1390945Notes

Reaction equation

HRID 1390945 reaction equation
[Cl:1][C:2]1[CH:3]=C(C=CC=1)C=CC(O)=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[S:20](Cl)(Cl)=O>N1C=CC=CC=1>[Cl:1][C:2]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([Cl:13])[C:15]=2[S:20][CH:3]=1

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 24386Thionyl ChlorideHCID 746313-(3-Chlorophenyl)prop-2-enoic acid

Product 1

HCID 86736353HCID 86736353, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 0.2 mole of 3-chlorocinnamic acid in a solution containing 200 ml. of chlorobenzene, 75 ml. of thionyl chloride and 2.0 ml of pyridine was heated at reflux for 72 hours and filtered while hot to remove insoluble material. The filtrate was concentrated to remove the solvent and the solid residue was recrystallized from toluene to give 3,7-dichlorobenzo[b]thiophene-;b 2-carbonyl chloride, m.p. 100°-102° C.

Workup

  1. additioncontaining 200 ml
  2. temperatureat reflux for 72 hours
  3. filtrationfiltered while hot
  4. customto remove insoluble material
  5. concentrationThe filtrate was concentrated
  6. customto remove the solvent
  7. customthe solid residue was recrystallized from toluene

Sources & evidence

ORD record
ord-d643e666cad54de4977b9381c82cf31c
Source dataset
uspto-grants-1979_02
Patent number
US04140785

Reaction notes

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