Pyridinium chloride → HCID 13290067, compound

HRID 652680Notes

Reaction equation

HRID 652680 reaction equation
[Cl:1][C:2]1[C:3]([O:20]C)=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=3[F:17])[S:7][C:6]=2[C:18]=1[Cl:19].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=3[F:17])[S:7][C:6]=2[C:18]=1[Cl:19]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290066HCID 13290066, compound

Product 1

HCID 13290067HCID 13290067, compoundYield 71.8%

Procedure

A mixture of 4.5 g of 6,7-dichloro-2-(2',6'-difluorophenyl)-5-methoxybenzo[b]thiophene and 45 g of pyridine hydrochloride is stirred at 190°-195° for 5 hrs and allowed to cool. While still fluid, the reaction mixture is poured onto 200 g of ice and stirred until thoroughly mixed. The aqueous mixture is extracted with three 200-ml portions of dichloromethane and the organic layers are combined, washed, dried over anhydrous magnesium sulfate and filtered. The solvent is removed to give a solid. The solid is recrystallized from ethyl ether-hexane to give 3.1 g of 6,7-dichloro-2-(2',6'-difluorophenyl)-5-hydroxybenzo[b]thiophene, mp 161°-162°.

Workup

  1. temperatureto cool
  2. stirringstirred
  3. additionuntil thoroughly mixed
  4. extractionThe aqueous mixture is extracted with three 200-ml portions of dichloromethane
  5. washwashed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent is removed
  9. customto give a solid
  10. customThe solid is recrystallized from ethyl ether-hexane

Sources & evidence

ORD record
ord-296110f5a38e4744a46f9cf2f3d3568a
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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