Reaction #49737

Reaction equation

Triphenyl phosphine

carbon tetrabromide

hexane

2-chloro-4-(sulphenyl)-benzaldehyde

→

1,1-dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene

Yield 62.8%

Solvents

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe resulting solid was filtered off
2. 2
   Washwashed with ether
3. 3
   OtherThe combined filtrates were evaporated to dryness
4. 4
   Otherthe residue was purified by chromatrography
5. 5
   Washeluted with hexane

Procedure

Triphenyl phosphine (2.5 g) was added to a stirred solution of carbon tetrabromide (1.48 g) in dichloromethane maintaining the temperature at 0° C. The mixture was stirred for 0.5 hours and 2-chloro-4-(sulphenyl)-benzaldehyde (1.0 g) was added. The resultant mixture was stirred for 0.5 hours and poured into hexane. The resulting solid was filtered off and washed with ether. The combined filtrates were evaporated to dryness and the residue was purified by chromatrography eluted with hexane to give 1,1-dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene (0.96 g) as a white solid, NMR (CDCl3) 2.45 (s,3H), 7.15(d,1H), 7.25(s,1H), 7.55(s,1H), 7.6(d,1H). By proceeding in a similar manner the following compound was prepared from the appropriately substituted starting material.

Source