Reaction #1519101

Reaction equation

Tetrabromomethane

7-oxanorborn-2-en-5-ylmethanol

triphenylphosphine

→

7-oxanorborn-2-en-5-yl-methyl bromide

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   OtherThe crude product was purified by flash chromatography (
4. 4
   workup.ADDITIONa 98:2 mixture of cyclohexane and ethyl acetate)
5. 5
   Other0.3 g (59% of theory) of the pure product were obtained

Procedure

Tetrabromomethane (1.161 g, 3.50 mmol) was added to a solution of 7-oxanorborn-2-en-5-ylmethanol (0.305 g, 2.50 mmol, from Example 2) in CH2Cl2 (12.5 ml). The solution was cooled to 0° C. and admixed with triphenylphosphine (1.836 g, 7 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The solvent was removed under reduced pressure and the remaining solid was taken up in cyclohexane. The crude product was purified by flash chromatography (using a 98:2 mixture of cyclohexane and ethyl acetate). 0.3 g (59% of theory) of the pure product were obtained. The product was stored under cool conditions with the exclusion of light.

Source