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Boron tribromide → 2-(4-Hydroxyphenyl)-6-(4-nonylphenyl)benzothiazole

HRID 1243268
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Reaktionsgleichung

Reaktionsgleichung von HRID 1243268
B(Br)(Br)Br.C([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:35][CH:34]=4)[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:20][CH:19]=1)CCCCCCCCCCC>ClCCl>[OH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[S:25][C:26]3[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:35][CH:34]=4)[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:22][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 219245242-(4-Dodecyloxyphenyl)-6-(4-nonylphenyl)benzothiazole

Produkt 1

HCID 1357617792-(4-Hydroxyphenyl)-6-(4-nonylphenyl)benzothiazoleAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Boron tribromide (0.53 cm3, 5.65×10−3 mol) was added dropwise to a cooled (0° C.) stirred solution of 2-(4-dodecyloxyphenyl)-6-(4-nonylphenyl)benzothiazole (2.25 g, 3.76×10−3 mol) in dichloromethane (100 cm3). The reaction mixture was stirred at room temperature overnight, then poured onto an ice/water mixture (200 g) and stirred (30 min). The reaction mixture was extracted with dichloromethane (2×75 cm3) and the combined organic layers were washed with brine (2×100 cm3) and dried (MgSO4). After filtration the solvent was removed under reduced pressure and the residue was purified by column chromatography [silica gel, ethyl acetate:hexane 1:1] followed by recrystallisation from ethyl acetate to yield 1.25 g (77.3%) of the desired product.

Aufarbeitung

  1. stirringstirred (30 min)
  2. extractionThe reaction mixture was extracted with dichloromethane (2×75 cm3)
  3. washthe combined organic layers were washed with brine (2×100 cm3)
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customthe residue was purified by column chromatography [silica gel, ethyl acetate:hexane 1:1]
  8. customfollowed by recrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-33520a08346448e58f6074d2f382d4e6
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07118787B2

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