Réaction #66038

ord-1484c856a3ab479daf9d33fbc09ffbee

Équation de réaction

BrBr
bromine
CC=CC(=O)c1ccc2c(c1)Cc1cc(C(=O)C=CC)ccc1S2
1-[7-(but-2-enoyl)-9H-thioxanthen-2-yl]-but-2-en-1-one
c1ccc2c(c1)Cc1ccccc1S2
thioxanthene
C/C=C/C(=O)Cl
crotonoyl chloride
[Al+3].[Cl-].[Cl-].[Cl-]
aluminium chloride
→
CC=CC(=O)c1ccc2sc3ccc(C(=O)C=CC)cc3c(=O)c2c1
2,7-bis-(but-2-enoyl)-thioxanthen-9-one

Réactifs

BrBr
bromine
CC=CC(=O)c1ccc2c(c1)Cc1cc(C(=O)C=CC)ccc1S2
1-[7-(but-2-enoyl)-9H-thioxanthen-2-yl]-but-2-en-1-one
c1ccc2c(c1)Cc1ccccc1S2
thioxanthene
C/C=C/C(=O)Cl
crotonoyl chloride
[Al+3].[Cl-].[Cl-].[Cl-]
aluminium chloride

Réactifs

CCCC[N+](CCCC)(CCCC)CCCC.[Br-]
tetra-n-butylammonium bromide

Solvants

ClCCl
dichloromethane

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrework-up and purification

Mode opératoire

To 1-[7-(but-2-enoyl)-9H-thioxanthen-2-yl]-but-2-en-1-one, which is synthesized by thioxanthene and crotonoyl chloride in the presence of aluminium chloride as described in WO2005-080337A1, dissolved in dichloromethane are added bromine (2.0 equiv.) and aqueous tetra-n-butylammonium bromide (0.5 equiv.). Stirring the reaction mixture at room temperature and succeeding extractive work-up and purification give 2,7-bis-(but-2-enoyl)-thioxanthen-9-one, which is transformed into the compound of example 9 as described in example 4.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08524425B2uspto-grants-2013_09