Water → 5-Bromo-6-fluorobenzo[b]thiophene-2-carboxylic acid

HRID 572414Notes

Reaction equation

HRID 572414 reaction equation
[Br:1][C:2]1[C:14]([F:15])=[CH:13][C:5]2[S:6][C:7]([C:9]([O:11]C)=[O:10])=[CH:8][C:4]=2[CH:3]=1.[Li+].[OH-].O>C1COCC1>[Br:1][C:2]1[C:14]([F:15])=[CH:13][C:5]2[S:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 70983611Methyl 5-bromo-6-fluorobenzo[b]thiophene-2-carboxylate

Product 1

HCID 709830545-Bromo-6-fluorobenzo[b]thiophene-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 25 for the preparation of I-25b above, methyl 5-bromo-6-fluorobenzo[b]thiophene-2-carboxylate (I-28b: 0.3 g, 1.038 mmol) in THF (10 mL) was hydrolyzed with LiOH (300 mg, 1.038 mmol) and water (2 mL) to afford 240 mg of the product (85% yield)

Workup

  1. customreagents and reaction conditions

Sources & evidence

ORD record
ord-55a529dccab142de815e4cf045c75148
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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