Reaktion #302844

ord-aa5a8eca694748f396195c01c6595b9e

Reaktionsgleichung

CC(=O)c1ccc(Br)s1
1-(5-bromothiophen-2-yl)ethanone
O=Cc1ccccc1Sc1ccccc1
4-(phenylthio)benzaldehyde
O=Cc1ccccc1Sc1ccccc1
formyl phenyl phenyl sulfide
[K+].[OH-]
potassium hydroxide
CO
methanol
O=C(/C=C/c1ccc(Sc2ccccc2)cc1)c1ccc(Br)s1
(E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one
O=C(/C=C/c1ccc(Sc2ccccc2)cc1)c1ccc(Br)s1
(E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl) prop-2-en-1-one

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIn FIG. 4, the synthesis scheme for PAG 16

Vorschrift

In FIG. 4, the synthesis scheme for PAG 16 is carried out as follows: A brominated acetylthiophene derivative, 1-(5-bromothiophen-2-yl)ethanone (14) is reacted with 4-(phenylthio)benzaldehyde (1) in the presence of methanol and potassium hydroxide at room temperature to form a precursor compound, (E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one (15). The precursor compound (15) is exposed to microwave heating at 125° C. in the presence of diphenyliodonium hexafluoro phosphate (V) (6) to form a photoacid generator, (E)-(4-(3-(5-bromothiophen-2-yl)-3-oxoprop-1-enyl)phenyl)diphenylsulfonium hexafluorophosphate(V), identified herein as PAG 16. The reactions are carried out by conventional heating (Δ) and microwave heating (MW) and the Quantum yield per molecule of PAG 16 is 71% for conventional heating (Δ) and 83% for microwave heating (MW).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08192590B1uspto-grants-2012_06