1,3-Benzodioxole-5-carbonyl chloride → HCID 22132652, compound

HRID 1857204Notes

Reaction equation

HRID 1857204 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1>C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:6]1[O:7][C:8]2[CH:9]=[CH:10][C:2]([C:1]([C:10]3[CH:9]=[CH:8][C:4]([OH:5])=[CH:3][CH:2]=3)=[O:11])=[CH:3][C:4]=2[O:5]1

Participants

4

Reactant 1

HCID 27347491,3-Benzodioxole-5-carbonyl chloride

Product 1

HCID 22132652HCID 22132652, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6212ChloroformSolvent

Procedure

4-Tri-n-butyltin-1-methoxymethylphenol (1.282 g) obtained in Example 22 and commercially available piperonyloyl chloride (664 mg) were dissolved in chloroform (5 ml), commercially available bis(triphenylphosphine)palladium(II) chloride (8 mg) was added, and the admixture was refluxed with heat overnight. The reaction mixture was partitioned in the same manner as described in Example 23, and the resulting ether layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue (1.030 g) was dissolved in tetrahydrofuran (2 ml), water (5 ml) and 6 N aqueous hydrochloric acid (12 ml) were added, and the admixture was refluxed with heat 10.5 hours. The reaction mixture was treated in the same manner as described in Example 123 to obtain 212 mg of the title compound (yield: 29%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat overnight
  3. customThe reaction mixture was partitioned in the same manner
  4. dry with materialthe resulting ether layer was dried with anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. distillationby reduced-pressure distillation
  7. dissolutionthe resulting residue (1.030 g) was dissolved in tetrahydrofuran (2 ml)
  8. additionwater (5 ml) and 6 N aqueous hydrochloric acid (12 ml) were added
  9. temperaturethe admixture was refluxed
  10. temperaturewith heat 10.5 hours
  11. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-c9d03bd8fa9546f696b4c74b5dc78767
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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