Potassium Hydroxide → [1,1'-Biphenyl]-3-thiol

HRID 522566

Reaktionsgleichung

Reaktionsgleichung von HRID 522566
C([S:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=S)OCC.[OH-].[K+]>C(O)C>[C:9]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=[CH:11][CH:12]=[C:7]([SH:6])[CH:8]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 10540302S-Biphenyl-3-yl O-ethyl carbonodithioate

Produkt 1

HCID 10821418[1,1'-Biphenyl]-3-thiolAusbeute 113,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 52a (1.1 g, crude compound) in ethanol (8 mL) was added potassium hydroxide (2.1 g, 12 mL) and heated to reflux for overnight. The solution was cooled to RT and the ethanol was evaporated under reduced pressure. The residue was dissolved in water and washed with diethyl ether (10 mL). The aqueous layer was acidified with 2 N HCl and extracted with diethyl ether (3×50 mL). The organic extracts were washed with water (50 mL), brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure to afford 0.85 g (77.3%) of crude biphenyl-3-thiol product (overall, 3 steps). Into a round-bottomed flask, stirred magnetically, were placed 0.1 g (1.04 mmol) of sodium tert-butoxide and 83 mg of copper iodide (0.43 mmol). After the reaction vessel was sealed, 0.13 g (0.71 mmol) of 4-methoxybenzenethiol and 0.19 g (0.65 mmol) of 5-iodo-1,2,3-trimethoxybenzene in 3.0 mL of toluene were injected through the septum. The reaction mixture was heated for overnight at 110° C. Purification was performed by flash chromatography, and an amorphous solid was obtained (40% yield). 1H NMR (500 MHz, CDCl3) δ 7.54-7.52 (m, 3H), 7.44-7.41 (m, 3H), 7.37-7.33 (m, 2H), 7.23 (s, br, 1H), 6.69 (s, 2H), 3.86 (s, 3H), 3.80 (s, 6H). MS (ESI) m/z 353.2 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for overnight
  3. customthe ethanol was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. washwashed with diethyl ether (10 mL)
  6. extractionextracted with diethyl ether (3×50 mL)
  7. washThe organic extracts were washed with water (50 mL), brine (50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b4bfc1ab6e024dd698205fe857c4f027
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334242B2

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