Carbon Dioxide → 2-Methyl-1-benzothiophene-7-carboxylic acid

HRID 1876362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876362
Br[C:2]1[C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:17](=[O:19])=[O:18]>O1CCCC1.C(OCC)C>[CH3:11][C:9]1[S:8][C:7]2[C:2]([C:17]([OH:19])=[O:18])=[CH:3][CH:4]=[CH:5][C:6]=2[CH:10]=1

Komponenten

6

Edukt 3

HCID 280Carbon DioxideHCID 126238737-Bromo-2-methyl-1-benzothiopheneHCID 178418339Butyllithium

Produkt 1

HCID 126239032-Methyl-1-benzothiophene-7-carboxylic acidAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The solution of 7-bromo-2-methylbenzo[b]thiophene (508) (0.908 g, 4.0 mmol) in tetrahydrofuran (16 mL) was cooled to −78° C. under nitrogen. n-butyllithium (2.40 mL, 6.0 mmol, 1.0M in Hexanes) was added dropwise. After the addition was complete, the reaction mixture was stirred at −78° C. for 1 h, then poured on to the mixture of dry ice in ethyl ether (30 mL). The reaction was stirred to reach room temperature for 5 hours, followed by washing with 1N HCl, brine and dried over sodium sulfate, filtered, and concentrated in vacuo. The obtained white solid was washed with hexanes to provide 2-methylbenzo[b]thiophene-7-carboxylic acid (509) (0.240 g, 31.2%). LC-MS ESI m/z: found 191.0 [M−H]−.

Aufarbeitung

  1. additionAfter the addition
  2. stirringThe reaction was stirred
  3. waitto reach room temperature for 5 hours
  4. washby washing with 1N HCl, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washThe obtained white solid was washed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f9b0d2dfb2e840bf8612157110decb21
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309600B2

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