Water → 5-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([C:10]([O:12]C)=[O:11])=[CH:9][C:5]=2[CH:4]=1.O.[OH-].[Li+].O>CO>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:5]=2[CH:4]=1Participants
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 300 mg of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, 66 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 tert-butyl methyl ether 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 280 mg of 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid (the present compound 1).
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 tert-butyl methyl ether 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-b20b741971b347bda8f24b5ccfe5d496
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09232792B2
Reaction notes
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