Hydrochloric Acid → HCID 22666473, compound

HRID 1007941Notes

Reaction equation

HRID 1007941 reaction equation
[F:1][C:2]1[C:3]([CH2:13][C:14]([O:16]C)=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[O:11][CH3:12].[OH-].[Na+].O.Cl>CO.C(OCC)(=O)C>[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][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22666383HCID 22666383, compound

Product 1

HCID 22666473HCID 22666473, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 39 mL of methanol is dissolved 3.87 g of methyl 2-(6-fluoro-7-methoxybenzo[b]thiophen-5-yl)-acetate, to which is added 6.6 mL of 3 mol/L aqueous solution of sodium hydroxide. The mixture is stirred at ambient temperature for 4 hours. The reaction mixture is concentrated under reduced pressure, the residue thus obtained is mixed with water and ethyl acetate, and pH is adjusted to 1 with 6 mol/L hydrochloric acid. The organic layer is separated, washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 2.80 g of 2-(6-fluoro-7-methoxybenzo[b]thiophen-5-yl)-acetic acid is obtained as a brown-colored crystalline product.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue thus obtained
  3. customThe organic layer is separated
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-7d6a2e24ce814158b83db8f0f31d8456
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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