wt/vol

 

wt/vol

MW

moles

density

equivs.

yield

I

6.7 mL

56.06

0.1003

0.839

1.0

 

II

5.0 mL

159.82

0.097

3.102

 

 

III

18 mL

148.20

0.1082

0.891

 

 

IV

13 mL

-

-

 

 

 

V

19.311 g

290.00

0.0666

 

 

(66%)

 

Procedure:  100 mL 3-neck flask, overhead stirrer, septum, thermometer, N2 inlet

                  Stirred 6.7 mL of acrolein (I) at 0 C as ~5.0 mL of Br2 was added dropwise over 30 min.  Stirred 15 min.  Added a solution of 18 mL of HC(OEt)3 in 13 mL of absolute EtOH dropwise over 10 min.  The bath was removed and the reaction was heated to 45 C.  After 2.5 h the reaction was cooled to rt.  The solvent and any remaining Br2 were removed by rotary evaporation and the product was isolated by distillation through a shortpath equipped with a vigreux (118 C, ~12 mm).  The product was a clear, pale yellow oil which darkened upon standing.