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Water → 4-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

HRID 589284
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 589284
[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]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18526201Methyl 4-(trifluoromethyl)-1-benzothiophene-2-carboxylate

Produkt 1

HCID 218411634-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acidAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ca55760306c54cc4b6121ca0af1e9e40
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09232792B2

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