Water → HCID 23568938, compound

HRID 2220310Notes

Reaction equation

HRID 2220310 reaction equation
[Cl:1][C:2]1[C:6]2[C:7]([F:13])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[S:4][C:3]=1[C:14]([O:16]C)=[O:15].O.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[C:6]2[C:7]([F:13])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[S:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 22171164Methyl 3-chloro-4-fluoro-7-methoxy-1-benzothiophene-2-carboxylate

Product 1

HCID 23568938HCID 23568938, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 3-chloro-4-fluoro-7-methoxy-1-benzothiophene-2-carboxylate (2.00 g, 7.29 mmol) was suspended in THF:H2O[10:1] and lithium hydroxide (260 mg) added, the resulting suspension was heated to 40° C. for 1 h. After cooling to room temperature the mixture was extracted with diethyl ether (50 mL) and the aqueous phase acidified to pH 2 and the solid collected by filtration and vacuum dried to give a white solid (1.09 g, 58%); δH (300 M , DMSO) 7.32-7.20 (1H, m, Ar), 7.15-7.05 (1H, dd, Ar), 3.98 (3H, s, OCH3).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionwas extracted with diethyl ether (50 mL)
  3. filtrationthe solid collected by filtration and vacuum
  4. customdried

Sources & evidence

ORD record
ord-ec0d6f3ef78f4f88a5f2bb6f712a3f34
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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