Boron trifluoride etherate → 6-Methoxy-1-benzothiophene

HRID 354076Notes

Reaction equation

HRID 354076 reaction equation
B(F)(F)F.CCOCC.C(O[CH:13](OCC)[CH2:14][S:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)C>C(Cl)Cl>[CH3:23][O:22][C:18]1[CH:19]=[CH:20][C:21]2[CH:13]=[CH:14][S:15][C:16]=2[CH:17]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 13642516(2,2-Diethoxyethyl)(3-methoxyphenyl)sulfane

Product 1

HCID 136342376-Methoxy-1-benzothiopheneYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of boron trifluoride etherate (14.45 mL, 115 mmol) in 2000 mL of methylene chloride stirring in a cold water bath 20° C. was added dropwise 1-(2,2-Diethoxy-ethylsulfanyl)-3-methoxy-benzene (28.2 gm, 110 mmol) dissolved in 500 mL of methylene chloride. The addition was complete in 3 hrs. and then the reaction was warmed to room temperature for a further 1.5 hrs. The reaction mixture was then quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was back extracted several times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel (using a gravity column) using hexanes as the eluant to yield 10.9 gm of the title compound.

Workup

  1. additionThe addition
  2. customThe reaction mixture was then quenched with saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel (

Sources & evidence

ORD record
ord-b270f99e13d44743839d10850f071d65
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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