Dimethylformamide → 2-[(3-Chlorophenyl)thio]-5-methoxybenzoic acid

HRID 1769185

Reaktionsgleichung

Reaktionsgleichung von HRID 1769185
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Br[C:21]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:21]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=2[C:23]([OH:25])=[O:24])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 162573-ChlorothiophenolHCID 899062-Bromo-5-methoxybenzoic acid

Produkt 1

HCID 3411532-[(3-Chlorophenyl)thio]-5-methoxybenzoic acidAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a mixture of 3-chlorothiophenol (20 g, 0.138 mol), and cupric acetate (1.8 g) and DMF (200 mL) was added K2CO3 (23 g). The mixture was heated to 150° C. for 15-20 minutes, then 2-bromo-5-methoxybenzoic acid (35.8 g, 0.155 mol) was added in portions. The mixture was heated overnight, poured into water (600 mL), filtered and the filtrate was treated with charcoal, filtered and diluted with HCl. The resulting precipitate was collected by filtration, washed with water, and dried at 50° C. in vacuo over P2O5 to afford 27.6 g of 2-[(3-chlorophenyl) thio]-5-methoxybenzoic acid.

Aufarbeitung

  1. temperatureThe mixture was heated overnight
  2. filtrationfiltered
  3. additionthe filtrate was treated with charcoal
  4. filtrationfiltered
  5. additiondiluted with HCl
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialdried at 50° C. in vacuo over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-5954937a007e44a4a44183c074f0b0b5
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380749

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