Reaction #302844

Reaction equation

1-(5-bromothiophen-2-yl)ethanone

4-(phenylthio)benzaldehyde

formyl phenyl phenyl sulfide

potassium hydroxide

methanol

→

(E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one

(E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl) prop-2-en-1-one

Conditions

Workup

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

Procedure

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).

Source