Hydrochloric Acid → HCID 12747903, compound

HRID 2083241Notes

Reaction equation

[Cl:1][C:2]1[C:14]([C:15](=[O:21])[C:16]2[S:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][C:5]2[CH2:6][CH:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:22].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.BrN1C(=O)CCC1=O.Cl>C(Cl)(Cl)(Cl)Cl.CS(C)=O.O>[Cl:1][C:2]1[C:14]([C:15](=[O:21])[C:16]2[S:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:22]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methyl 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxylate (3.6 g., 0.01 mole) in carbon tetrachloride (100 ml.) containing a few crystals of benzoyl peroxide is treated with N-bromosuccinimide (1.8 g., 0.01 mole) then refluxed for one hour. The reaction mixture is cooled, filtered free of succinimide and the solvent distilled at reduced pressure to leave a yellow residual oil comprised of a mixture of methyl 2(and 3)-bromo-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate which is dissolved in dimethylsulfoxide (25 ml.) treated with 1,5-diazobicyclo(4.3.0)-5-nonene (1.3 g., 0.01 mole), stirred at 25° C. for two hours in an inert atmosphere, diluted with water (100 ml.) and acidified with hydrochloric acid to give methyl 6,7-di chloro-5-(2-thenoyl)benzofuran-2-carboxylate wich melts at 184°-7° C. after recrystallization from acetonitrile-H2O.

Workup

temperaturethen refluxed for one hour
temperatureThe reaction mixture is cooled
filtrationfiltered free of succinimide
distillationthe solvent distilled at reduced pressure
customto leave a yellow residual oil

Sources & evidence

ORD record: ord-0e6dea2af01947b09afc88cc2059a10a
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04085117

Reaction notes

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