2-Furancarbonyl chloride → HCID 12747893, compound

HRID 262391Notes

Reaction equation

HRID 262391 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].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](Cl)=[O:21].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[C:13]([C:20]([C:16]2[O:15][CH:19]=[CH:18][CH:17]=2)=[O:21])=[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 682422-Furancarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 98160656,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic Acid

Product 1

HCID 12747893HCID 12747893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred mixture of 6,7-dichloro-2,3-dihydro-benzofuran-2-carboxylic acid (3.3 g.), furan-2-carbonyl-chlorine (3.6 g.) and 200 ml. methylene chloride, protected from the atmosphere with a calcium chloride tube is added anhydrous aluminum chloride (3.7 g.) over a one-half hour period. The reaction solution is stirred 18 hours at 25° C. and then refluxed for 1 hour. The solvent is removed and the residue added to ice water (200 ml.) and hydrochloric acid (20 ml.). The product is extracted into ether, washed with water, then extracted into aqueous sodium bicarbonate (200 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-furoyl)-benzofuran-2-carboxylic acid melts at 166° C. after crystallization from acetonitrile/n-butyl chloride.

Workup

  1. stirringThe reaction solution is stirred 18 hours at 25° C.
  2. temperaturerefluxed for 1 hour
  3. customThe solvent is removed
  4. additionthe residue added to ice water (200 ml.) and hydrochloric acid (20 ml.)
  5. extractionThe product is extracted into ether
  6. washwashed with water
  7. extractionextracted into aqueous sodium bicarbonate (200 ml.) from which the sodium salt of the product
  8. customprecipitates
  9. customThe sodium salt of the product is placed in a separatory funnel with dilute hydrochloric acid (100 ml.) and ether (100 ml.)
  10. stirringshaken until the solid
  11. dissolutiondissolves
  12. washThe ether solution is washed with water, brine
  13. dry with materialdried over magnesium sulfate
  14. distillationthe ether distilled at reduced pressure
  15. customThe 6,7-dichloro-2,3-dihydro-5-(2-furoyl)-benzofuran-2-carboxylic acid melts at 166° C. after crystallization from acetonitrile/n-butyl chloride

Sources & evidence

ORD record
ord-0d9ee77eaf554e16bd333a37c190ffee
Source dataset
uspto-grants-1979_05
Patent number
US04154742

Reaction notes

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