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Water → 7-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

HRID 589286
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 589286
[F:1][C:2]([F:17])([F:16])[C:3]1[C:8]2[S:9][C:10]([C:12]([O:14]C)=[O:13])=[CH:11][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:8]2[S:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18526203Methyl 7-(trifluoromethyl)-1-benzothiophene-2-carboxylate

Produkt 1

HCID 179796237-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acidAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 800 mg of methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, 154 mg of lithium hydroxide monohydrate, 4 ml of water and 12 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 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 632 mg of 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid (the present compound 4).

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 tert-butyl methyl ether 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-64ea382c66a94c9d837d6c641bcc757d
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09232792B2

Notizen zur Reaktion

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