Water → 6-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid

HRID 589282Notes

Reaction equation

HRID 589282 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([O:13]C)=[O:12])[S:8][C:7]=2[CH:15]=1.O.[OH-].[Li+].O>CO>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[S:8][C:7]=2[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18526202Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate

Product 1

HCID 179795236-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 400 mg of methyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, 105 mg of lithium hydroxide monohydrate, 3 ml of water and 9 ml of methanol was stirred at 75° C. for 2 hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added water, and then washed with tert-butyl methyl ether 3 times. To the aqueous layer was added concentrated hydrochloric acid, and then extracted with chloroform 3 times. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 355 mg of 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid (the present compound 2).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added water
  4. washwashed with tert-butyl methyl ether 3 times
  5. additionTo the aqueous layer was added concentrated hydrochloric acid
  6. extractionextracted with chloroform 3 times
  7. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-048cfd55641c4ce383a340b22f2db110
Source dataset
uspto-grants-2016_01
Patent number
US09232792B2

Reaction notes

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