Water → 6-Bromo-1-benzothiophene-2-carboxylic acid

HRID 572400

Reaction equation

HRID 572400 reaction equation
O[Li].O.O.C[O:6][C:7]([C:9]1[S:13][C:12]2[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:11]=2[CH:10]=1)=[O:8].C(OCC)(=O)C>C1COCC1>[Br:18][C:15]1[CH:16]=[CH:17][C:11]2[CH:10]=[C:9]([C:7]([OH:8])=[O:6])[S:13][C:12]=2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 224740786-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

Product 1

HCID 135679806-Bromo-1-benzothiophene-2-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (1.85 g, 44 mmol) and water (20 mL) were added to a stirred solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid methyl ester (I-25a: 2.4 g, 8.85 mmol) in THF (25 mL) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was concentrated, acidified with 2N HCl, filtered and the residue was washed with n-hexane to afford 1.9 g of the product (84% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-29183dc67e464649866eb49aebd32d4a
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Linked notes

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