Water → 5-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

HRID 2271307Notes

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]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 10.0 g of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, 1.80 g of lithium hydroxide monohydrate, 30 ml of water and 90 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 obtained residue was added water, and 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 9.10 g of 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
additionTo the obtained 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-701126159e044d88a57218f1a9553e71
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09119396B2

Reaction notes

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