Bromine → 3-[(4-Bromo-2,5-dimethylphenyl)thio]propanoic acid

HRID 1602773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602773
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[Br:15]Br>ClCCl>[Br:15][C:6]1[C:5]([CH3:8])=[CH:4][C:3]([S:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[CH:7]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 167883143-(2,5-Dimethyl-phenylsulfanyl)-propionic acid

Produkt 1

HCID 196075383-[(4-Bromo-2,5-dimethylphenyl)thio]propanoic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

25.23 g (0.12 mol) of the title compound of Example 1, Step A was dissolved in 250 mL of dichloromethane and cooled to 5° C. A solution of 19.12 g (0.12 mol) of bromine in 25 mL of dichloromethane was added dropwise over 45 minutes, keeping the reaction temperature at 5° C. The reaction was then allowed to warm to room temperature, diluted with 200 mL of dichloromethane and washed twice with 400 mL of water. The organice layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 34.35 g of the title compound of step A as a white solid melting at 105-107° C. 1H NMR (CDCl3): δ2.33 (s,3H), 2.34 (s, 3H), 2.67 (t, 2H), 3.10 (t, 2H), 7.18 (s, 1H), 7.36 (s, 1H).

Aufarbeitung

  1. customat 5° C
  2. temperatureto warm to room temperature
  3. washwashed twice with 400 mL of water
  4. customThe organice layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3ded7d574ea9484d809cdf4bae618c6e
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985799

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