Sulfuric Acid → HCID 178422466, Verbindung

HRID 1042527

Reaktionsgleichung

Reaktionsgleichung von HRID 1042527
[Br:1][C:2]1[C:3]([OH:17])=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Si](OCC)(OCC)(OCC)OCC.[CH:31]([C:34]1[CH:40]=[CH:39][CH:38]=[C:37]([CH:41]([CH3:43])[CH3:42])[C:35]=1[NH2:36])([CH3:33])[CH3:32].OS(O)(=O)=O>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](/[C:9](=[N:36]/[C:35]2[C:37]([CH:41]([CH3:42])[CH3:43])=[CH:38][CH:39]=[CH:40][C:34]=2[CH:31]([CH3:33])[CH3:32])/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[OH:17]

Komponenten

5

Edukt 4

HCID 1118Sulfuric AcidHCID 6517TetraethoxysilaneHCID 32484DiisopropylanilineHCID 12925474(3-Bromo-2-hydroxy-5-methylphenyl)(phenyl)methanone

Produkt 1

HCID 178422466HCID 178422466, VerbindungAusbeute 69,1 %

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

In 50 mL Claisen's flask in argon atmosphere, a mixture of 13.5 g (46.3 mmol) of 26, 20.2 g (97.2 mmol) of Si(OEt)4, and 9.03 g (50.9 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.37 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 35 hr, and the formed ethanol was slowly distilled off. Later, 300 mL of cold water was added, and the product was extracted with 2×100 mL of diethyl ether. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.). This procedure gave 14.4 g (69%) of the title product.

Aufarbeitung

  1. distillationthe formed ethanol was slowly distilled off
  2. additionLater, 300 mL of cold water was added
  3. extractionthe product was extracted with 2×100 mL of diethyl ether
  4. extractionThe combined extract
  5. dry with materialwas dried over K2CO3
  6. customevaporated to dryness
  7. customThe product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.)

Quellen und Nachweise

ORD-Eintrag
ord-81172488656d4ea890cc22abb85e795d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557936B2

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