Triethylamine → HCID 13170366, Verbindung

HRID 736860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736860
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].C(N(CC)CC)C.[Si:32]([O:39][C:40]1[CH:47]=[CH:46][C:43](C=O)=[CH:42][CH:41]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>ClCCl>[Br:21][C:20]([Br:24])=[CH:1][C:47]1[CH:46]=[CH:43][CH:42]=[CH:41][C:40]=1[O:39][Si:32]([C:35]([CH3:36])([CH3:37])[CH3:38])([CH3:33])[CH3:34]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Produkt 1

HCID 13170366HCID 13170366, VerbindungAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Triphenylphosphine (3.44 g, 13.1 mmol) was dissolved in dichloromethane (25 ml) in nitrogen atmosphere, carbon tetrabromide (2.18 g, 6.56 mmol) was added little by little under cooling with ice, and triethylamine (4.4 ml, 26.2 mmol) was dropwise added, followed by stirring for 10 minutes. Then, under cooling with ice, a dichloromethane solution (20 ml) of 4-(tert-butyldimethylsilyloxy)benzaldehyde (10.0 g, 73.4 mmol) prepared in 1) was dropwise added, followed by stirring for 1 hour. Silica gel (50 g) was added to the reaction solution, the reaction solution was concentrated under reduced pressure to dryness, and the resulting product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1, containing 0.1% v/v triethylamine) to give 1,1-dibromo-2-(tert-butyldimethylsilyloxyphenyl)ethylene (2.77 g, 81%) as a pale yellow oily substance.

Aufarbeitung

  1. additionwas added little by little
  2. additionwas dropwise added
  3. temperatureThen, under cooling with ice
  4. additionwas dropwise added
  5. stirringby stirring for 1 hour
  6. additionSilica gel (50 g) was added to the reaction solution
  7. concentrationthe reaction solution was concentrated under reduced pressure to dryness
  8. customthe resulting product was purified by silica gel column chromatography (hexane
  9. additionethyl acetate=20:1, containing 0.1% v/v triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-48d234ce93d74c7181df844808c40222
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595415B2

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