Acetic Acid → HCID 13290012, compound

HRID 1903446Notes

Reaction equation

HRID 1903446 reaction equation
[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]2[CH:9](O)[CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:7][C:6]=2[C:17]=1[Cl:18].B(F)(F)F.CCOCC.C(O)(=O)C>O.[OH-].[Na+]>[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]2[CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:7][C:6]=2[C:17]=1[Cl:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 20197925HCID 20197925, compound

Product 1

HCID 13290012HCID 13290012, compoundYield 30.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5.0 g of 6,7-dichloro-2,3-dihydro-3-hydroxy-5-methoxy-2-phenylbenzo[b]thiophene, 10 ml of boron trifluoride etherate and 20 ml of glacial acetic acid is refluxed for 1 hour. The mixture is cooled, diluted with water and basified with dil sodium hydroxide solution. Extraction with dichloromethane followed by column chromatography over silica (50% dichloromethane in hexane) gives 1.45 g of 6,7-dichloro-5-methoxy-2-phenylbenzo[b]thiophene, mp 144°-145°.

Workup

  1. temperatureis refluxed for 1 hour
  2. temperatureThe mixture is cooled
  3. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-cce25aeb82f34830b207e8c74becfec2
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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