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

HRID 1465989Notes

Reaction equation

HRID 1465989 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-305b789ca44a46fb86a2b0e4825f2a4b
Source dataset
uspto-grants-2015_04
Patent number
US09000008B2

Reaction notes

Loading…