Boron trifluoride etherate → HCID 13952872, compound

HRID 370979Notes

Reaction equation

HRID 370979 reaction equation
[CH2:1]([C:5]1(Cl)[S:9][C:8]2[C:10]([Cl:17])=[C:11]([Cl:16])[C:12]([O:14][CH3:15])=[CH:13][C:7]=2[C:6]1(Cl)O)[CH2:2][CH2:3][CH3:4].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C>[Cl:16][C:11]1[C:12]([O:14][CH3:15])=[CH:13][C:7]2[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[S:9][C:8]=2[C:10]=1[Cl:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium Hydroxide2×HCID 20197908HCID 20197908, compound

Product 1

HCID 13952872HCID 13952872, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5.0 g of 2-n-butyl-6,7-dichloro-2,3-dichloro-3-hydroxy-5-methoxybenzo[b]thiophene in 25 ml of glacial acetic acid is added 6.5 ml of boron trifluoride etherate, with stirring. The mixture is heated on a steam bath until dissolution occurs and is stirred at room temperature for one hour. A mixture of 20 ml of 10% sodium hydroxide solution and 50 mg of ice is added followed by 50% sodium hydroxide solution to pH 7. The mixture is extracted with 3×100 ml-portions of ether. The ether extracts are washed with water, dried and concentrated to give an oil. The oil is chromatographed on 100 g silica gel column using a 9:1 hexane dichloromethane system as the eluant. Evaporation of the eluant gives 2.3 g of 6,7-dichloro-2-n-butyl-5-methoxybenzo[b]thiophene or an oil.

Workup

  1. temperatureThe mixture is heated on a steam bath until dissolution
  2. stirringis stirred at room temperature for one hour
  3. additionis added
  4. extractionThe mixture is extracted with 3×100 ml-portions of ether
  5. washThe ether extracts are washed with water
  6. customdried
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe oil is chromatographed on 100 g silica gel column
  10. customEvaporation of the eluant

Sources & evidence

ORD record
ord-43d3092773b748108651d57ce6ebf464
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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