2-Thiophenecarbonyl chloride → HCID 12747881, compound

HRID 262389Notes

Reaction equation

HRID 262389 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:14].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](Cl)=[O:21].[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[Cl:1][C:2]1[C:13]([C:20](=[O:21])[C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:14]

Participants

5

Reactant 3

HCID 789282-Thiophenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 98160656,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic Acid

Product 1

HCID 12747881HCID 12747881, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a well stirred mixture of 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid (2.6 g.) and thiophene-2-carbonyl chloride (4 ml.) protected from the atmosphere with a calcium chloride tube is added anhydrous aluminum chloride (6.0 g.) over a one-hour period. The reaction mixture is heated at 80°-90° C. for 31/2 hours then poured into ice water (100 ml.) and hydrochloric acid (10 ml.). The product is extracted into ether, washed with water, then extracted into aqueous sodium bicarbonate (100 ml.) from which the sodium salt of the product precipitates. The sodium salt of the product is placed in a separatory funnel with dilute hydrochloric acid (100 ml.) and ether (100 ml.) and shaken until the solid dissolves. The ether solution is washed with water, brine, dried over magnesium sulfate and the ether distilled at reduced pressure. The 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxylic acid melts at 187° C. after crystallization from butyl chloride.

Workup

  1. customprotected from the atmosphere with a calcium chloride tube
  2. temperatureThe reaction mixture is heated at 80°-90° C. for 31/2 hours
  3. extractionThe product is extracted into ether
  4. washwashed with water
  5. extractionextracted into aqueous sodium bicarbonate (100 ml.) from which the sodium salt of the product
  6. customprecipitates
  7. customThe sodium salt of the product is placed in a separatory funnel with dilute hydrochloric acid (100 ml.) and ether (100 ml.)
  8. stirringshaken until the solid
  9. dissolutiondissolves
  10. washThe ether solution is washed with water, brine
  11. dry with materialdried over magnesium sulfate
  12. distillationthe ether distilled at reduced pressure
  13. customThe 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxylic acid melts at 187° C. after crystallization from butyl chloride

Sources & evidence

ORD record
ord-0d9e10b8bb7046b5a44d52b7ad22f56a
Source dataset
uspto-grants-1979_05
Patent number
US04154742

Reaction notes

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