Potassium Hydroxide → 4-Bromo-3-methylbenzene-1-thiol

HRID 422554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422554
CN(C)C(=O)[S:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[CH:6]=1.[OH-].[K+]>CO>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([SH:4])=[CH:6][C:7]=1[CH3:12]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 86620291S-4-bromo-3-methylphenyl dimethylcarbamothioate

Produkt 1

HCID 156611054-Bromo-3-methylbenzene-1-thiolAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of S-4-bromo-3-methylphenyl dimethylcarbamothioate (4.56 g, 16.6 mmol) and potassium hydroxide (3.27 g, 58.2 mmol) in MeOH was heated at 90° C. for 1 hour. The mixture was cooled to RT and concentrated. The residue was redissolved in DCM and aqueous sodium bicarbonate (sat.) and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography (100% hexanes) to afford 2.84 g of 4-bromo-3-methylbenzenethiol as a pale yellow oil.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in DCM
  4. customaqueous sodium bicarbonate (sat.) and the layers were separated
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel chromatography (100% hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6add02a9154c413ab9c2978e3d096b19
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101612B2

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