Boron trifluoride etherate → HCID 13290025, compound

HRID 370960Notes

Reaction equation

HRID 370960 reaction equation
[Cl:1][C:2]1[C:3]([O:18][CH3:19])=[CH:4][C:5]2[CH:9](O)[CH:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[S:7][C:6]=2[C:16]=1[Cl:17].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([O:18][CH3:19])=[CH:4][C:5]2[CH:9]=[C:8]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[S:7][C:6]=2[C:16]=1[Cl:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 13290179HCID 13290179, compound

Product 1

HCID 13290025HCID 13290025, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.5 g of 6,7-dichloro-2-cyclopentyl-2,3-dihydro-3-hydroxy-5-methoxybenzo[b]thiophene and 10 ml of glacial acetic acid containing 5 ml of boron trifluoride etherate is warmed on a steam bath for 15 minutes and allowed to stand overnight. The mixture is poured into a chilled solution of dilute sodium hydroxide and the organic material is extracted into ether. Washing with water, followed by drying over anhydrous magnesium sulfate and evaporation in vacuo, gives 2.0 g of wax-like crystals. Recrystallization from ether-hexane gives 1.8 g of 6,7-dichloro-2-cyclopentyl-5-methoxybenzo-[b]thiophene as fine needles, mp 59.5°-60°.

Workup

  1. temperatureis warmed on a steam bath for 15 minutes
  2. extractionthe organic material is extracted into ether
  3. washWashing with water
  4. dry with materialby drying over anhydrous magnesium sulfate and evaporation in vacuo
  5. customgives 2.0 g of wax-like crystals
  6. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-1859287386f144719a068ee3d2e0d322
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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