Water → HCID 22666411, compound

HRID 1007942Notes

Reaction equation

HRID 1007942 reaction equation
[F:1][C:2]1[C:3]([CH2:13][C:14]([OH:16])=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[O:11]C.B(F)(F)F.O>C(Cl)Cl>[F:1][C:2]1[C:3]([CH2:13][C:14]([OH:16])=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6356Boron trifluorideHCID 22666473HCID 22666473, compound

Product 1

HCID 22666411HCID 22666411, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In 17.4 mL of methylene chloride is suspended 1.74 g of 2-(6-fluoro-7-methoxybenzo[b]thiophen-5-yl)-acetic acid, to which is added 13.8 mL of 1 mol/L solution of boron trifluoride in methylene chloride. The mixture is stirred at ambient temperature for 3 hours. The reaction mixture is introduced into a mixture of methylene chloride and water and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 1.42 g of 2-(6-fluoro-7-hydroxybenzo[b]thiophen-5-yl)-acetic acid is obtained as a gray-colored crystalline product.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-fdfef0f149c543aba2f24a1dd9050b48
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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