Potassium Hydroxide → 6-Bromo-1-benzothiophene-2-carboxylic acid

HRID 55771

Reaction equation

HRID 55771 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11]C)=[O:10])[S:8][C:4]=2[CH:3]=1.[OH-].[K+]>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 224740786-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

Product 1

HCID 135679806-Bromo-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.0 g (14.8 mmol) of methyl 6-bromo-1-benzothiophene-2-carboxylate in 40 ml of a 1:1 mixture of THF and 2 N potassium hydroxide solution is stirred at room temperature for 2 h. The solvent is removed in vacuo, and the residue is acidified with concentrated hydrochloric acid. The resulting precipitate is filtered off with suction, washed with water and dried in vacuo at 50° C. 3.55 g (93.5% of theory) of the desired product are obtained.

Workup

  1. customThe solvent is removed in vacuo
  2. filtrationThe resulting precipitate is filtered off with suction
  3. washwashed with water
  4. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-195c3d7f9ab44d679c042dadfc5e6873
Source dataset
uspto-grants-2016_09
Patent number
US09433614B2

Linked notes

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