Water → 4-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:11]2[CH:10]=[C:9]([C:12]([O:14]C)=[O:13])[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.O.[OH-].[Li+].O>CO>[F:16][C:2]([F:1])([F:17])[C:3]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1Participants
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 290 mg of methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, 60 mg of lithium hydroxide monohydrate, 2 ml of water and 6 ml of methanol was stirred at 75° C. for 1 hour. 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 240 mg of 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid (the present compound 3).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- additionTo the residue was added water
- washwashed with tert-butyl methyl ether 3 times
- additionTo the aqueous layer was added concentrated hydrochloric acid
- extractionextracted with chloroform 3 times
- washThe combined organic layer was washed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ca55760306c54cc4b6121ca0af1e9e40
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09232792B2
Reaction notes
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