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

HRID 572409Notes

Reaction equation

HRID 572409 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([Br:15])[C:12]([F:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].O>C1COCC1>[Br:15][C:11]1[C:12]([F:14])=[CH:13][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[S:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 70982166Methyl 6-bromo-5-fluorobenzothiophene-2-carboxylate

Product 1

HCID 709820566-Bromo-5-fluorobenzo[b]thiophene-2-carboxylic acidYield 90.9%

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, 6-bromo-5-fluoro-benzo[b]thiophene-2-carboxylic acid methyl ester (I-27b: 0.3 g, 1.0 mmol) in THF (10 mL) was hydrolyzed with LiOH (87 mg, 2.04 mmol) and water (2 mL) to afford 250 mg of the product (yield 88%)

Workup

  1. customreagents and reaction conditions

Sources & evidence

ORD record
ord-05605056f18444218277b12f33947421
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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