Boron trifluoride etherate → HCID 13290014, compound

HRID 370947Notes

Reaction equation

HRID 370947 reaction equation
[Cl:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]2[CH:9](O)[CH:8]([CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]2[CH:9]=[C:8]([CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 13952868HCID 13952868, compound

Product 1

HCID 13290014HCID 13290014, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.7 g of 6,7-dichloro-2,3-dihydro-3-hydroxy-5-methoxy-2-methylbenzo[b]thiophene in 20 ml of glacial acetic acid containing 5 ml of boron trifluoride etherate is warmed on a steam bath for 5 min. to form a clear solution. After stirring at room temperature for 1 hour, the solution is poured into an ice-cold solution of 10% sodium hydroxide. The organic materials are extracted 3 times with ether, dried and concentrated under vacuum. The reddish brown residue is purified by dissolving it in ether and passing it through an alumina column packed with ether. Elution with ether gives 2.1 g of 6,7-dichloro-5-methoxy-2-methylbenzo[b]thiophene as off-white crystals, mp 113°-114°.

Workup

  1. customto form a clear solution
  2. extractionThe organic materials are extracted 3 times with ether
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe reddish brown residue is purified
  6. dissolutionby dissolving it in ether
  7. washElution with ether

Sources & evidence

ORD record
ord-0a22c365492d4c8c8d127b7f07b55677
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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