Carbon tetrabromide → 2-(3,5-Dimethoxyphenylthio)benzyl bromide

HRID 2299184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299184
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14]O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][Br:40])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 118079672-(3,5-Dimethoxyphenylthio)benzyl alcohol

Produkt 1

HCID 155124432-(3,5-Dimethoxyphenylthio)benzyl bromideAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(3,5-Dimethoxyphenylthio)benzyl alcohol (7.9 g) was dissolved in methylene chloride (40 ml), then triphenylphosphine (11.2 g) and carbon tetrabromide (11.2 g) were added thereto, the mixture was stirred at room temperature for ten minutes, diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1) to give 2-(3,5-dimethoxyphenylthio)-benzyl bromide (9.53 g, yield of 98%).

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-af1ea5a612f849688c6f977097bf3822
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495592B1

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